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Classical Methods in Structure Elucidation of Natural Products
Classical Methods in Structure Elucidation
of Natural Products
R. W. Hoffmann
Author All books published by Wiley-VHCA are carefully
produced. Nevertheless, authors, editors, and
Prof R. W. Hoffmann publisher do not warrant the information
University of Marburg contained in these books, including this book,
Department of Chemistry to be free of errors. Readers are advised to keep
Hans-Meerwein-Straße 4 in mind that statements, data, illustrations,
35032 Marburg procedural details or other items may
Germany inadvertently be inaccurate.
Cover Library of Congress Card No.: applied for

Getty #: 539191220 / Jill Ferry Photography
British Library Cataloguing-in-Publication Data
A catalogue record for this book is available
from the British Library.
Bibliographic information published by

the Deutsche Nationalbibliothek
The Deutsche Nationalbibliothek
lists this publication in the Deutsche
Nationalbibliografie; detailed bibliographic
data are available on the Internet at
<http://dnb.d-nb.de>.
© 2018 Wiley-VHCA AG, Seehofstrasse 6,

CH-8008 Zürich, Switzerland
All rights reserved (including those of

translation into other languages). No part of
this book may be reproduced in any form – by
photoprinting, microfilm, or any other means
– nor transmitted or translated into a machine
language without written permission from the
publishers. Registered names, trademarks, etc.
used in this book, even when not specifically
marked as such, are not to be considered
unprotected by law.
Print ISBN: 978-3-906390-73-4

ePDF ISBN: 978-3-906390-79-6
ePub ISBN: 978-3-906390-78-9
Mobi ISBN: 978-3-906390-80-2
obook ISBN: 978-3-906390-81-9
Typesetting SPi Global Private Limited,

Chennai, India
Printing and Binding
Printed on acid-free paper

v
Contents
Preface vii
Hundred Years of Structure Elucidation 1
Part I Compounds with only Oxygen Functionalities 11
1 Ascorbic Acid 13
2 Hinokitiol 19
3 Cantharidin 27
4 Camphor 35
5 α-Terpineol 47
6 Lactaroviolin 53
7 Santonin 59
8 Estrone 75
9 α-Tocopherol 87
Part II Compounds with Nitrogen and Oxygen Functionalities 95
10 Pyridoxine 97
11 Muscarine 105
12 Lupinine 113
13 Lysergic Acid 121

vi Contents
14 Riboflavin 131
15 Cocaine 137
16 Quinine 151
17 Colchicine 167
18 Luciferin 181
19 Strychnine 191
Part III Compounds with Additional Functionalities 207
20 Biotin 209
21 Thiamine 221
22 Griseofulvin 229
Part IV Compounds without Heteroatom-Functionalities 237
23 Decacyclene 239
24 Carotene 243
Part V Can You Do it Yourself? 251
25 Penicillin 253
Index 261
vii
Preface
It is a well‐accepted standard in the education of scientists to advise the novices

that they should not hesitate to question the validity of “established” facts. Facts
and “dogmas” in science acquire the status of being “established” by no longer
being questioned. Doubting established facts in an experimental science requires
checking whether the underlying experimental data and deductions are rigorous
and unambiguous.
The structures of many natural products are depicted in standard textbooks of
Organic Chemistry as “established facts.” But how solid are the experimental
data that predicate a particular structure given for a natural product? In the case
of natural products, the structures of which were elucidated in the period 1860–
1960 by classical chemical methods, the lines of evidence are frequently buried
under a plethora of degradation studies, that is, investigations that repeatedly led
into culs‐de‐sac and to revised structure assignments.
It is the aim of this treatise to bring those lines of evidence to light for a number
of representative natural products. The choice of the examples is subjective and
arbitrary, dictated by the pleasure to recover fundamental achievements of
Organic Chemistry. In doing so, the author gained further profound respect for
the intellectual achievements of past generations of chemists, who carried out
these structure elucidations with minimal experimental tools.
This work pays tribute to the great scientists of the past generation, whose
contributions are no longer appreciated by the present generation of young
chemists. Those presently being educated, for example, in the United States or
Japan, frequently lack a linguistic background to read and appreciate the contri-
butions of German, French, or Italian chemists of the nineteenth and twentieth
centuries published in their native tongues. It is all the more important to high-
light their accomplishments at least by presenting some examples.
Finally, I had the feeling to be prepared for such a task, as my chemistry educa-
tion comprised just the methods and reasoning of classical chemistry that form
the content of this treatise. To prevent any misunderstanding, this treatise does
not give the history of structure elucidation of particular natural products.
Rather, the results from historic experiments are combined to derive a line of
evidence for the structures that are accepted as “established” today. The line of
evidence may follow the path put forward by the original contributors. In some
viii Preface
instances, however, the experimental facts have been combined to another,

hopefully shorter, line of evidence. Eventually, it is the aim to put the reader into
a position to trace the “facts behind the established structure assignments” of
some important natural products.
July 24, 2014 Reinhard W. Hoffmann

1
Hundred Years of Structure Elucidation
Those natural products, the structures of which appear in the textbooks, are the
basic representatives that form the core of organic chemistry. Most of these
structures have been elucidated in the period that present‐day chemists consider
the “Stone Age” of organic chemistry. All the more, chemists should be willing to
question the validity of these structure assignments. How solid are the facts that
support the structure assignment? How cogent are the connections of these facts
to the final conclusion? Surprisingly, very little knowledge on the structure eluci-
dation of those natural products prevails at present; reason enough to bring
these achievements of the previous generations of chemists to light again.
Hence, this treatise deals with exemplary structures elucidated in the hundred
years from 1860 to 1960. While the facts presented are historic, this is not a his-
tory of the structure elucidations. This would be much too detailed, as the struc-
ture elucidations of most of the products covered here were highly ramified with
many culs‐de‐sac.
Rather, one should justify the limits 1860 and 1960. The year 1960 approximately
marks the change from classical structure elucidation by degradation to the era in
which structure elucidation is mainly based on spectroscopic evidences and X‐ray
crystallography. Since it is the emphasis of this treatise to address classical struc-
ture elucidation, efforts made after 1960 are only considered in exceptional cases.
The other limit, 1860, has to do with the notion of structure. Prior to the
advent of structural theory [1], there was no conceptual framework to address
Figure 1
Classical Methods in Structure Elucidation of Natural Products. First Edition, R. W. Hoffmann.

© 2018 Wiley-VHCA AG, Seehofstrasse 6, CH-8008 Zürich, Switzerland.
2 Hundred Years of Structure Elucidation
the “structure” of a compound. This framework was provided by Kekulé (1857)

[2], Couper (1858) [3], and Butlerov (1859) [4, 5]. The insight that the C‐atom
has four valencies and that C─C bonds form the backbone of organic com-
pounds constituted the basis of the structural theory; it is the distinct connec-
tivity between the atoms that defines the structure of an organic compound [5].
This theory made it for the first time comprehensible why (and how many)
isomeric substances could exist for a given elemental composition of a
compound.
Information Box 1
Structure Elucidation;
What is STRUCTURE ??
Structure Theory: Stereochemistry:

Kekulé (1857) Le Bel (1874)
Cooper (1858) van't Hoff (1875)
Butlerov (1861)
Of similar importance was the foundation of stereochemistry by LeBel [6]

(1874) and van’t Hoff [7] (1875), making it comprehensible why (and how many)
“stereoisomeric” substances could exist for a given constitution of a compound.
Subsequently, the determination of such connectivities, that is, the structure of
any compound of interest, became the predominant task of organic chemistry.
Yet, this task constituted a challenge of unprecedented dimensions for the chem-
ists at the end of the nineteenth century, because the structure of a new com-
pound had to be related to that of structurally known compounds in, what one
could call, a self‐consistent network of information. Obviously, at the beginning,
there were only a rather small number of structurally characterized compounds,
which fortunately expanded rapidly with every decade of dedicated work.
Obviously, in the course of time, it was increasingly easier to reach a known com-
pound upon degradation of an unknown compound.
The situation was aggravated by the fact that the tools to elucidate structures of a
given compound, that is, to establish the relation to other known compounds, were
deplorably limited. Indeed, all that chemists had at their disposal were next to sim-
ple glassware, a balance, a Bunsen burner, and a few thermometers. All the more,
one has to admire and respect the achievements of the chemists of that period.
The concept of structure could be attributed only to a “uniform” compound,
that is, the sample to be studied had to be homogeneous. In the absence of any
chromatographic or spectroscopic means to establish homogeneity, there was
only the criterion of the invariance of the melting point. This means that the
melting point of the sample did not change upon repeated crystallization, prefer-
ably from different solvents.
As a next step in structure elucidation, the elemental composition was to be
established, both qualitatively and quantitatively, to arrive at the molecular
formula. Quantitative combustion analysis provided the ratio of the elements in
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Number of known Organic Compounds

1400000
1200000
1000000
800000
600000
400000
200000
0
< < < < < < < < < <
1870 1880 1890 1900 1910 1920 1930 1940 1950 1960
Figure 2
(a) (b) (c)
Figure 3 Source: (a) ref. [16] (b) With kind permission of Dr. Timo Mappes, www.musoptin.com;
(c) ref. [17].
the compound, that is, (CxHyNzOw)n. In those days, the methods to arrive at the
molecular formula, that is, to determine n by vapor‐density measurement, cry-
oscopy, or ebullioscopy, were known. Nevertheless, in most cases, n was assumed
to be 1, and molecular weights were determined only when in doubt.
The next step in structure elucidation concerned the kind of functional groups
present. The nature of the elements present in the compound provided a hint, as
to which qualitative tests [8] for functional groups should be conducted.
The information reached at this level (melting point, molecular formula, and
functional groups present) was sufficient to decide whether one deals with a
known or a new compound, by consulting a compendium [9] of (common)
known compounds, listed according to the melting point, and searching for a hit
with the same characteristics.
Information Box 2
Structure Elucidation;
Initial steps
Homogeneity constant melting point
Elemental Composition empirical formula

Molecular weight
Test for Functional Groups
Is Compound known??
Enough information for checking
Figure 4 CRC Handbook of Chemistry and Physics.
When the compound at hand was not listed in the standard compendia, one
would consult Beilsteins Handbuch der Organischen Chemie. There, compounds
are listed in a systematic manner, according to which, for each compound with a
given molecular formula and distinct functional groups, there is a unique place,
where the compound should be listed. One could in this way check whether a
compound with the same melting point was listed or which isomeric compounds
of the proper composition were known, leaving the remaining isomers as possi-
ble candidates. For such a search, there was a limitation due to the closing date of
a particular volume. To acquire information after such a closing date, one would
have to search the formula registers of the annual volumes of the Chemisches
Zentralblatt and later of Chemical Abstracts and, from these, the abstracts, and
then the original papers to find out whether a compound with the same charac-
teristics as that of the one at hand has already been described. A major hurdle in
Figure 5 Beilsteins Handbuch der Organischen Chemie.

Source: With kind permission of Engelbert Zass, Zürich.
doing this was the fact that the nomenclature used for individual compounds has
changed several times over the years.
One aspect became immediately evident in doing such searches: the range of
melting points, commonly between 20 and 320 °C, is with about 150 data points
not sufficient to distinguish ten thousands of compounds. Hence, there was the
requirement of preparing (crystalline) derivatives of the compound at hand and
to compare their melting points as well with the published data. Actually, the
compendia and Beilstein list the derivatives and their melting points right along-
side the data of the parent compound. However, a single derivative may not be
enough to differentiate between two known compounds, as seen in the case of
the 3‐ and 4‐isopropyl‐cyclohexanones. Hence, it became customary to prepare
at least two derivatives of a parent compound for definitive identification. When
the melting points matched, identification was considered as accomplished.
Information Box 3 Beilsteins Handbuch der Organischen Chemie, 2. Supplementary work,

1948, 7, p.31.
At this point, the conclusion could as well be that the compound at hand is not
known and that the structure had to be determined by chemical means. This
endeavor would start with a degradation of the compound to smaller (hopefully
known) compounds. Degradation relied on oxidative cleavage at or near the
functional groups present in the molecule, such as ozonolysis of C═C bonds, oxi-
dative cleavage at C═O groups effected with refluxing HNO3, alkaline KMnO4, or
CrO3 in acetic acid. Admittedly, this approach is crude, very similar to the attempts
to learn something about a Chinese porcelain figurine in a dark room by knocking
it to pieces, collecting them, and to examine them later by light. But this approach
was the only one chemists could apply at the end of the nineteenth century.
Accordingly, Williams recommended [10]:
Information Box 4
if it is not a known compound

start degradation:
by cleavage at the functional groups
typically refluxing HNO3
alkaline KMnO4
CrO3 in acetic acid
refluxing aq. Ba(OH)2
Such degradation studies required large amounts of the material to be studied in

order to obtain in the end not only something that crystallized but also the product
in sufficient amounts to be characterized and to be – when necessary – degraded
further. Experimental sections typically read as follows [11, 12]:
It is obvious that these experimental aspects restricted structure elucidation to

those compounds that could be obtained – from nature or otherwise – in large
quantities.
Degradation thus furnished a small number of fragments that reflect the
position(s) of the functional groups in the parent molecule. Nevertheless, con-
clusions regarding the structure of the original molecule remained difficult.
Fortunately, the kind of transformation effected by a particular degradation
reaction, for example, the ozonolysis of a C═C bond, may serve as a guideline in
reconstructing the original structure.
Information Box 5
Stepwise degradation until known compounds are reached
generates an incomplete set of pieces of a structure puzzle
? how to put them together ?
need information on the backbone by (reductive) defunctionalization.
distillation from Zn-dust at 400°C
Even then, there would usually remain manifold possibilities to arrange the frag-
ments in order to arrive at a potential structure of the original compound. Hence,
there was the necessity to gain information on the nature of the backbone of the
parent compound. The task is to rid the backbone of the attached h eteroatoms,
that is, the functional groups. Baeyer was the one that introduced the Zn‐dust
distillation for this purpose [13]. This treatment soon became the standard tech-
nique to unveil the backbone of aromatic compounds. Much later, this technique
was complemented for alicyclic compounds by the Se‐dehydrogenation [14], a
method by which alicyclic compounds were converted to aromatic compounds
with a related backbone.
Once the backbone of a compound was recognized with the aid of one of
these methods, it was usually possible on the basis of the fragment compounds
from the degradation studies to allocate the position(s) of the functional groups
at the backbone, leading to a rational proposal for the structure of the com-
pound at hand.
Such a structural proposal was, however, nothing more than a working hypothesis.
Confirmation of such a hypothesis had then to be reached by synthesis. Obviously,
the planning of such a synthesis benefited from all the information on the peculiari-
ties of the compound and its degradation products acquired by the degradation stud-
ies. Nevertheless, the synthesis had to fulfill the requirements of providing proof for
the proposed structure, implying that it could enlist only such reactions, which were
well established and reliable in their course. Moreover, the synthesis had to proceed
only in short straightforward steps, the results of which could be individually checked
by going one step backward. But such restrictions were really seminal in developing
the art of synthesis in the late nineteenth century.
The practical aspects of structure elucidation relied almost exclusively on
melting points for the characterization of compounds and mixed melting points
for the identification of compounds. Hence, crystallization of a compound from
the crude products of a reaction – chromatography had not been invented
yet – became the essential capability of the chemists at that time. In turn, com-
pounds that did not crystallize had only a small chance to be investigated in
detail. Nevertheless, even with all these limitations, chemists were remarkably
successful to establish the structures of almost all abundant natural products.
Very little progress though, if at all, was made in determining the stereostruc-
ture of the compounds of interest. The relative configuration of substituents at a
C═C bond ((E) or (Z)), or a ring (cis or trans), could be addressed by attempting
to link these substituents forming a new cycle, such as a five‐membered cyclic
anhydride or lactam. This would succeed only when the substituents were in a
cis‐disposition.
Otherwise, an attempt could be made in a top‐down approach to excise from
the molecule by degradation the substructure containing the stereogenic
center(s) and to try to correlate this fragment compound obtained with a com-
pound of known configuration. In turn, there was the option of a bottom‐up
approach in synthesizing the various stereoisomers and to see which one matched
the compound of interest. But this option was generally foiled by the inability of
effecting stereoselective synthesis with a foreseeable stereochemical outcome.
Rather, reactions that generated stereogenic centers were in most cases stereo‐
unselective, leading to mixtures of (dia)stereoisomers, which had to be separated
by fractional crystallization in a laborious manner. Even when separated, the
compounds would not reveal their configuration by themselves.
Therefore, in the first 100 years after structural theory had been conceived,
neither the analytical methods nor those of stereoselective synthesis were apt to
readily address the stereostructure of natural products. This situation changed
dramatically with the advent of spectroscopic methods for structure elucidation,
which occurred in the time span of 1930–1960. From then on, structure elucida-
tion became the task of spectroscopy, rendering chemical means of structure
elucidation more and more obsolete.
There was also an important corollary regarding synthesis: confirmation of a

hypothetical structure was no longer solely the task of synthesis. Natural‐product
synthesis was freed from the chains to be structure‐proof and could develop to a
creative field of chemistry in its own right [15].
References
1 Staab, H.A. (1958) Angew. Chem., 70, 37–41.
2 (a) Kekulé, A. (1857) Ann. Chem. Pharm., 104, 129–150; (b) Kekulé, A. (1858)
Ann. Chem. Pharm., 106, 129–159.
3 (a) Couper, M.A. (1858) C.R. Hebd. Seances Acad. Sci., 46, 1157–1160;
(b) Couper, A.S. (1859) Ann. Chem. Pharm., 110, 46–51.
4 Butlerow, A. (1859) Ann. Chem. Pharm., 110, 51–66.
5 Konovalov, A.I. (2011) The Butlerov Theory in ‘Special print for the International
Congress on Organic Chemistry’, Kazan.
6 LeBel, J.‐A. (1874) Bull. Soc. Chim. Paris, 22, 337–347.
7 van’t Hoff, J.‐H. (1875) Ann. Chem. Pharm., 23, 295–301.
8 Shriner, R.L., Fuson, R.C., Curtin, D.Y., and Morrill, T.C. (1980) The Systematic
Identification of Organic Compounds, 6th edn, John Wiley & Sons, Inc.,
New York.
9 (a) Utermark, W. and Schicke, W. (1963) Schmelzpunkttabellen Organischer
Verbindungen, 2nd edn, Akademie Verlag, Berlin; (b) Weast, R.C. and Astle,
M.J. (eds) (1982) CRC Handbook of Chemistry and Physics, 63rd edn, CRC
Press, Boca Raton, FL.
10 Baldwin, R.S. (1975) J. Nutr., 105, 1–14.
11 Weidel, H. (1874) Liebigs Ann. Chem., 173, 76–116.
12 Andreocci, A. (1895) Gazz. Chim. Ital., 25(Pt. 1), 452–568.
13 Baeyer, A. (1866) Liebigs Ann. Chem., 140, 295–296.
14 Plattner, P.A. (1942) Angew. Chem., 55, 131–137; 154‐158.
15 Eschenmoser, A. (1974) Naturwissenschaften, 61, 513–525.
16 Dr. Guenther, http://de.wikipedia.org/wiki/Datei:Analysenwaage2.jpg
17 G.M. Hofman, https://commons.wikimedia.org/wiki/File:Maxima‐
Thermometer.jpg. Licensed under CC‐BY‐SA 3.0
11
Part I
Compounds with only Oxygen Functionalities

13
Ascorbic Acid
Figure 1.1 Albert Szent‐Györgyi

(b. 16.9.1893–d. 22.10.1986), in 1911,
started to study medicine at the
University of Budapest. This was
followed by his cosmopolitan years in
Prague, Berlin, Hamburg, Leiden,
Groningen, Cambridge, and Rochester,
before accepting a chair at the
University of Szeged in 1930. In 1947, he
moved to the Marine Biology
Laboratories in Woods Hole (MA) in the
United States. In 1937, Albert Szent‐
Györgyi was awarded the Nobel Prize for
Medicine for his research on vitamin C.
Source: J.W. McGuire, https://commons.
wikimedia.org/wiki/File:Albert_Szent-
Gy%C3%B6rgyi_cropped.jpg. CC-public
domain.
A strongly reducing substance, C6H8O6, was isolated from the adrenal glands
in 1928 by Szent‐Györgyi [1]. This substance was later identified as vitamin C,
the essential food constituent, the lack of which leads to scurvy (in French,
“scorbut”). Hence, this substance was given the name ascorbic acid [2].

14 1 Ascorbic Acid
Figure 1.2 (a) Fruits containing

vitamin C. (b) Signs of scurvy.
Source: (a) Serg64/Shutterstock, www.
gettyimages.com (b) Dorling
Kindersley Ltd, Gütersloh, Germany.
(a) With kind permission of Dorling
Kindersley Ltd, Gütersloh, Germany.
Scurvy
Pale skin
Sunken
Loss of eyes
teeth
(b)
The highly oxygenated nature of this substance indicated a relationship with car-
bohydrates, and, indeed, ascorbic acid showed a positive Molisch test. The
molecular formula suggests ascorbic acid to be a dehydrogenated (−4H) hexose.
Information Box 1 Molisch Test for Pentoses and Hexoses [3, 4].
Pentoses and hexoses, therefore carbohydrates in general are dehydrated

by sulfuric acid to generate furfural or hydroxymethyl-furfural. When this is
effected in the presence of a phenol, such as α-naphtol, condensation to
give a red or violet colored triphenyl-methane dye is initiated.
OH OH
+ 2
R O R
O O
R = H, CH2OH
OH
1.1 Preliminary Findings. Upon treatment with chloro(triphenyl)methane,

ascorbic acid readily formed a trityl ether [5]. Hence, ascorbic acid contains a
primary alcohol function. Upon treatment with HCl, ascorbic acid formed fur-
fural quantitatively [6]. Accordingly, ascorbic acid contains at least five C‐atoms
in a linear chain.
H H
HO
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1 Ascorbic Acid 15
Ascorbic acid readily formed an acetonide [7]. It should, therefore, be a 1,2‐ or

1,3‐diol. Finally, it was established with a Zerewitinoff test that ascorbic acid con-
tains four H‐atoms active toward Grignard reagent CH3MgI [8].
Information Box 2 Zerewitinoff Test for Active Hydrogen [9].
Methyl-Grignard reagents such as CH3MgI react with all compounds

containing a –OH, –NH2, –NH, –SH, –C≡CH group under evolution of
methane. The methane evolved can be quantified volumetrically to
determine the number of -XH groups in the compound investigated.
CH3MgI + R-XH CH4 + R-X-MgI
As the name implies, ascorbic acid is acidic, with a pKA value of 4.1 [5]. Ascorbic
acid thus readily yielded a sodium salt C6H7O6Na [8]. Upon reaction of ascorbic
acid with CH2N2, two (acidic) OH groups were methylated to give a dimethoxy
compound 1.1 C8H12O6 [8, 10].
Ascorbic acid as well as its sodium salt gave a strong positive result for the Fe3+
color test for enols [8], whereas that of the dimethoxy compound was negative.
Therefore, at least one of the acidic H‐atoms in ascorbic acid belongs to an enol,
and the other one may belong to a second enol or to a carboxylic acid.
1.2 Cleavage of ascorbic acid into smaller fragments was accomplished by oxi-
dation: upon oxidation with NaOI, 1 equiv. of oxalic acid was obtained [6].
Oxidation of ascorbic acid by KMnO4 furnished oxalic acid and a 2,3,4‐trihy-
droxybutanoic acid 1.2; Scheme 1.1 [6, 11].
KMnO4
C6H8O6 HOCH2 – CHOH–CHOH–COOH + HOOC–COOH
1.2
Scheme 1.1
1.3 Since there are two diastereomeric forms of 2,3,4‐trihydroxybutanoic acid,

the relative configuration of 1.2 was addressed at this point. To this end, com-
pound 1.2 was permethylated with (MeO)2SO2/KOH, and the methyl ester
obtained was converted with NH3 to a crystalline amide (Scheme 1.2).
This amide turned out to be different from the known amide of erythro‐2,3,4‐tri-
methoxy‐butanoic acid. Hence, compound 1.2 ought to be the threo‐diastereomer
thereof [11].
H H OH
HO
HO
16 1 Ascorbic Acid
COOH CONH2 CONH2

1) (MeO)2SO2
CHOH CHOMe is not H OMe
CHOH 2) NH3 CHOMe H OMe
CH2OH CH2OMe CH2OMe
1.2
CONH2
HNO3 HCl Ag2O NH3 H OMe
MeOH MeI MeOH MeO H
CONH2
Scheme 1.2
The threo‐configuration was established by oxidizing compound 1.2 with

HNO3 (Scheme 1.2). This led to a tartaric acid, which was identified after esteri-
fication, O‐methylation, and amide formation as being the (R,R)‐tartaric acid.
These findings established the following partial structure of ascorbic acid:
H H O(H)
HO
HO
1.4 The as‐yet‐unidentified right‐hand part of ascorbic acid contains one more
C‐atom and three O‐atoms including the enol function, identified under Section 1.1.
Further evidence was sought by methylating (blocking) all OH‐functions followed
by cleavage of the C═C bond, starting with the dimethoxy compound 1.1 C8H12O6
described under Section 1.1, which still contained two OH groups. Thus, com-
pound 1.1 was methylated with MeI/Ag2O to give a tetramethoxy compound
C10H16O6 (1.3) [11].
The latter should still contain the enolic C═C bond, which could be cleaved
with O3 to give a neutral compound C10H16O8 (1.4) (Scheme 1.3). Compound 1.4
retained all 10 C‐atoms of its precursor 1.3. Therefore, the enolic C═C bond in
the tetramethoxy compound C10H16O6 must have been part of a ring! Ozonolysis
of an enol ether gives rise to an ester. To cleave the ester moiety, compound 1.4
was treated with NH3, resulting in oxamide and the amide 1.5 of a hydroxy‐
dimethoxy‐butanoic acid [11].
In this transformation, three CO─NH2 moieties have been generated. Therefore,
1.4 must have contained three ester functions. Yet, bookkeeping of the atoms
COOMe COONH2
CHO Me NH3 CHO Me O
O CHO H + H2N
CHO NH2
MeOH
CH2OMe OMe CH2OMe O
O
C10H16O8 1.4 1.5
Scheme 1.3
1 Ascorbic Acid 17
allows for only two methyl esters in compound 1.4. Hence, the third ester func-
tion should be a lactone unit. Accordingly, the precursor tetramethoxy compound
C10H16O6, the permethylated ascorbic acid, 1.3, must have been a lactone and a
dimethyl ether of an ene‐diol.
MeO OMe
C C
O
CHO
CHO Me
C10H16O6 CH2OMe 1.3
1.5 All that remained at this point was to determine the ring size of the lactone. This
could be determined by locating the position of the free OH group in the hydroxy‐
dimethoxy‐butanamide 1.5. To this end, compound 1.5 was subjected to Weerman
degradation by the action of NaOCl [12]. The liberation of cyanate in this process
evidenced the presence of an α‐hydroxy‐carboxamide in 1.5. Hence, the lactone ring
must have been five‐membered, and already present in ascorbic acid, the structure of
which was thus established as the enol form of 3‐keto‐l‐gulonolactone:
H H O OH
HO
OH
HO
Information Box 3 Weerman Degradation [12].
In the Hofmann degradation a carboxamide R-CONH2 is cleaved to R-NCO

and CO2. Weerman found that when the residue R contains an α-hydroxy-
function, the resulting isocyanate undergoes hydrolysis to cyanate and an
aldehyde. This reaction has been applied to the stepwise degradation of
carbohydrates.
O O
R OX R R NCO R + NCO
NH2 NH
OH OH X −HX OH O
References
1 Szent‐Györgyi, A. (1928) Biochem. J., 22, 1387–1409.
2 Szent‐Györgyi, A. and Haworth, W.N. (1933) Nature, 131, 24.
3 Molisch, H. (1886) Monatsh. Chem., 7, 198–209.
4 Bredereck, H. (1931) Ber. Dtsch. Chem. Ges., 64, 2856–2859.
5 Karrer, P., Schwarzenbach, G., and Schöpp, K. (1933) Helv. Chim. Acta, 16, 302–306.
6 Cox, E.G., Hirst, E.L., and Reynolds, R.J.W. (1932) Nature, 130, 888.
18 1 Ascorbic Acid
7 von Vargha, L. (1932) Nature, 130, 847.

8 Karrer, P., Salomon, H., Schöpp, K., and Morf, R. (1933) Helv. Chim. Acta, 16,
181–183.
9 Zerewitinoff, T. (1907) Ber. Dtsch. Chem. Ges., 40, 2023–2031.
10 Micheel, F. and Kraft, K. (1933) Z. Physiol. Chem., 215, 215–224.
11 Herbert, R.W., Hirst, E.L., Percival, E.G.V., Reynolds, R.J.W., and Smith, F. (1933)
J. Chem. Soc. (London), 1270–1290.
12 Weerman, R.A. (1917) Recl. Trav. Chim. Pays‐Bas, 37, 16–51.
19
Hinokitiol
Figure 2.1 Chamaecyparis taiwanensis.

Source: Karlostachys, https://commons.
wikimedia.org/wiki/
File:Chamaecyparis_formosensis_
karlostachys_1.jpg. Licensed under
CC‐BY SA 3.0.
Hinokitiol is an antifungal and strongly antibacterially active terpene origi-

nally isolated from Taiwan‐grown hinoki trees Chamaecyparis taiwanensis. Its
history has been summarized [1] as follows.
T. Nozoe …isolated an enolic compound, hinokitiol, from the heartwood of the
Taiwan cypress and showed its molecular formula C10H12O2 in 1938. As the spec-
tral instruments, which are extensively used currently, were then unavailable, the
structural elucidation relied on chemical methods, which generally required a
large sample and work over a protracted period. The research was interrupted by
World War II. Because cypress oil can be used as a substitute for motor fuel, the
Japanese army ordered the Taipei factory of Takasago Perfumery Company to

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In glancing over the current issue of The Courier-Tribune I notice that the
good citizens of Seneca are putting on a Biblical show this week. That’s
fine. Whenever I hear of home talent aspiring to portray those ancient
characters on the stage I become interested right away. It recalls to mind the
time when I myself was, briefly, in the cast of a local entertainment of that
sort held in the old school house here in Wetmore many, many years ago.
It was a show the likes of which Wetmore had never had before, nor since—
a show that stands out in memory as the one classic of the times—a show
that rocked the whole countryside, rocked it with near volcanic convulsions.
Considering the extraordinary performers and the conduct of an audience
which ran wild, this little review is not offered as something worthy of
emulation. Nor is it to be construed as criticism. Rather, it is something to
be contrasted with the newer interpretations and renditions, something to be
compared with present-day reactions as against old-time unbridled
responses.
As aforesaid, with other local talent—grownups, and some lesser lights,
including an injection of members of “that tanyard gang”—I was cast for a
minor part in that show. To give you the right slant on this last mentioned
group of my theatrical co-workers, I should say here that my father operated
a tannery in the old days, and “the gang” — frequenters of the yard—
included just about all the happy-go-lucky youth of the town, vividly alive,
and callow. Collectively, we made quite a record—something short of
enviable, it now pains me to relate.
It was my dear old Sunday School superintendent who had selected me for
one of her characters in this Biblical show. I had been marvelous—so she
said—in her Sunday School, committing and reciting as many as twenty
Bible verses on a Sunday morning, for which I would sometimes be given a
little up-lift card. She said that my good work in her Sunday School was
guarantee enough for her that I would handle the part assigned me
creditably. I would not need to attend rehearsals. All that I should do was to
have my good mother make for me a heterogeneous coat according to
specifications. She would instruct me at the last minute so that I wouldn’t
forget.
I was to take the part of Joseph—Joseph, the boy. And, although a bit
irregular, and I might say diabolically devised, to save the stage-carpenter
the trouble of making a pit to cast me into, one of my Hebrew brothers—I
think it would have been Judah, who, off stage, was a big Swede — was to
have batted me on the “bean” so that I couldn’t protest when he and my
other naughty brothers would sell me to the Egyptians, and thus banish me
to the Land of Bondage. I wouldn’t need to rehearse? Oh, no, of course not!
And as it turned out I didn’t perform, either.
The show was going strong. The audience applauded and yelled itself
hoarse. After a particularly exciting scene, Rolland Van Amburg, the town
clown, jumped up from his seat and yelled, “It’s the best thing Wetmore
ever had—I’ve had my money’s worth already! Come and get another
quarter!” Van was ably assisted in this demonstration by one William
Morris, leading merchant.
The sponsoring lady was in high glee—happy daze. She said to her puppets,
“It’s taking! Oh, dear children, we must give them this one again!” She
flitted about from one to another, saying, “Oh, girls, please do hurry!”
The scene which had so excited Van was a tableau draped in naught but thin
mosquito bar and set off by the best soft mellowing light effect that could
be had with the oil-burning lamps, depicting some Biblical event with
strictly private and as time goes quite modern interpretations. Embroidered
beyond the original concept, it exhibited in silhouette some of Wetmore’s
fairest damsels—some who will read this and blush—in an amazing state of
dishabille. I should like to—and probably will—hear from Montana and
Idaho, and even faraway Hollywood, on this statement.
A wag in the audience who was not man enough to show himself, like Van,
yelled, “Take down the bars!” The audience roared! The sponsoring lady
beamed! Things got to going so good for the director that she began pulling
surprises on the performers. Wholly without warning, she ordered Clifford
Ashton to take off his shirt. That young Englishman, ever obliging and
obedient, had about completed the job when Dr. Thomas Milam cried out in
his most dramatic voice, “Put that shirt back on, you idiot!”
The woman, who was my Sunday School superintendent, overhearing the
Doctor’s remark, forthwith gave another curt command: “Off with that
shirt, Clifford—off with that shirt!” The voice carried, full and resonant,
through the calico partitions to the rear of the auditorium. That command
became a phrase which was hurled at Clifford as long as he lived here. He is
now in Seattle, Washington.
As already stated, I was to have taken the part of Joseph. I had a sort of
vague idea that my beautiful coat of variegated hues was to have been torn
from my person by my brothers to show to my old man as evidence of a lie
they were going to tell him. And not knowing what turn of mind the now
deliriously happy director would take next, I beat it—went outside and
thought I would see the show through the green shutters which covered the
old school house windows.
Outside, I found that other deserters had preceded me. Bill McVay, a grown
young man, bewhiskered for the occasion, with a flowing white beard the
likes of which has seldom been seen on this earth since the days of Moses,
said, in his drawling voice, “I could drink all the whisky the old town’s got
and it wouldn’t faze me—but that thing has bumped me off my feet. She’ll
have to get someone else to take my part.”
Actually, I was afraid to remain in the cast, fearing, the way things were
happening, fast and furious like, that I might be persuaded against my will
to appear before that hilariously responsive audience with greatly reduced
apparel. I really was in a dangerous spot. The plot called for partial forced
disrobement. Knowing the hyenas who posed as my brothers, and knowing
also that those brothers had caught the spirit of the producer in a large way,
I had the feeling that when they would have finished with me, working in
that free atmosphere, that it would have been sans pants for little Johnny.
It should be borne in mind that the director of this very extraordinary show
was an extremely odd woman, very religious, and sincere—and, having
ideas of her own, she had the courage to mirror them bounteously in her
work.
The show was all right, of course. Biblical, and all that. And, viewed with
an eye for the beautiful, it was all that Van said it was. But coming as it did
in an age of many clothes for women, it was a revelation.
ODD CHARACTERS —
COLORFUL, PICTURESQUE
Not Hitherto Published—1947.
By John T. Bristow
The discussion of odd characters was going strong when I entered the
corner grocery store one evening. I did not join in the discussion for the
simple reason that the range of observations did not go far enough back to
take in the really odd ones—as I knew them. Had I told what I’m going to
tell now, without supporting evidence it would, perhaps, have branded me
as a prevaricator, and I wouldn’t have liked that. But I’m taking no chances
now. Supporting evidence is at hand.
Speaking of odd characters, Wetmore had ‘em in the old days—in numbers.
In truth, this assertion takes in just about everyone, except of course Thee
and Me—that is, if Thee are still living. The odd characters dominating this
story were Mr. O. Bates, Mr. Peter Shuemaker, and Mr. Jim Riley.
But first, an opening paragraph introducing a fourth character that shall be
nameless—that is, in spelled out letters. I think I shall call my man Mr.
June, and guarantee that I have not missed his real name more than thirty
days. Also, he had a brother in the business, and the firm-name was June
Bros.—only this is one month away from it, in the springtime.
Mr. June came into my printing office to arrange for some advertising—and
also to get a load of fire insurance. I wrote fire insurance on the side. He
was bringing a stock of clothing from his store in Atchison, and putting it in
the Bates grocery store below the printing office, in the Bleisener block.
Mr. June inquired of me about our fire fighting facilities, and as to whether
or not we had waterworks. When I told him we had no waterworks and
practically no fire protection, he almost let his portly Jewish self fall off the
chair. He promised, “The first thing you should have waterworks when I
come.”
I told Mr. June that he was moving in with a man who had the agency for a
sure-shot fire fighting hand grenade. This seemed to hit him a little off
guard—but he rallied, and said he would investigate. It is presumed that his
investigation was satisfactory. He moved in right away. Also, he might have
heard about Mr. O. Bates’ ineffective demonstration with his hand grenades.
They had “fizzled” on him a while back.
The clothing stock had been in the building only about sixty days when a
mysterious fire occurred at 11:45, in the night—old time. It started in the oil
room under the stairs leading up to my office. I was working late that night,
with a shaded coal oil lamp on my desk. When I looked away from my
work, I was startled by a solid wall of smoke which had come up through a
stovepipe hole in the rear end of the room and stood only a few feet away
from my desk. Alex Hamel had been working with me, but he had left the
office some time before that. Also, Myrtle Mercer had been working that
night, and I had gone out to take her home—leaving the office in total
darkness while I was away.
Alex Hamel and Bill McAlester, a barber, were first to show up after I had
rushed out and yelled “Fire!” It was not long before a crowd had assembled.
Some gave their attention to the fire in the building, while others rushed up
stairs to my office, against my protest. There was no fire in the printing
office. “Chuck” Cawood dashed a bucket of water on my shaded coal-oil
lamp, and rushed out of the room, yelling, “I put it out—I’ve put it out!”
Chuck’s water had also ruined an order of printed stationery ready for
delivery. Others milled about in the dark and “pied” several galleys of type
we had set for the paper which was to come out the next day. The clothing
stock was carried to the street—and the fire was put out before it had done
much damage. Since there were two occupants of the store room, no one
could say with certainty whose fire it might have been.
The Jew’s insurance was canceled in due course. He said, “If I don’t got
insurance, I’ll not stay in a town which don’t got waterworks.” I reminded
him that he still had Mr. O. Bates, with his hand grenades. It was but a short
while before this that Mr. O. Bates had acquired the agency for his hand
grenades. He planned a demonstration in the public square, by making a
pyramid of wooden boxes, about ten feet high, early in the afternoon as a
sort of advertisement for the event to take place after dark. This advertising
stunt brought him humiliating repercussions.
The square was filled with people. Mr. O. Bates, a gabby auctioneer who
really knew how to make a spiel, gave them a good one. He said, “Ladies
and gentlemen. I have here the greatest fire extinguisher ever devised! But
you don’t have to take my word for this! You shall see with your own eyes!
Why, my friends, I wouldn’t hesitate one moment about building my
bonfire right up against my own home.”
Then he backed off a few paces from the burning boxes and threw a
grenade at the fire—but it failed to connect with the solid bumpboard,
which had been placed in the center to break the glass bottles, and passed
through the mass as a dud. He then tried again, hitting the bumpboard, but
instead of quenching the fire, it made a decided spurt upwards. Then, with a
huge grunt, Bates, threw them in as fast as he could, resulting in further
spurts of blaze upward — up, up, and up!
It was then boos for Mr. O. Bates. He was a sadly confused man, numb with
bewilderment. He stammered, “I’ll fetch a man here who’ll show you that
they will do the trick.” At a lesser publicized exhibition, Bates—and his
man—had extinguished the fire quickly. Rumor had it that “Frosty” and
“Cooney” had emptied the chemicals out of his grenades, and had filled
them with coal oil.
Mr. O. Bates had unbounded faith in his grenades. He actually wanted to
build his bonfire almost smack-up against the frame hotel building on the
corner where Harry Cawood’s store is now. But “Uncle” Peter Shuemaker
wouldn’t stand for that. “Uncle” Peter was a wiry little man of Pennsylvania
Dutch ancestry—much set in his ways, with a quick tongue with which to
defend himself. He was always on the defense.
“Frosty” Shuemaker had said, with reason, “Granddad, don’t you let that
old windjammer light his fire near the hotel. You don’t know what might
happen,” and “Uncle” Peter had snapped, “Goway, Forrest—who’s asking
you for advice?” But, I think, “Uncle” Peter had “smelled a mouse.”
Mr. O. Bates — pompous, windy, and positive — told “Uncle” Peter that
the proposed demonstration would do his hotel no more harm than for him
to allow Jim Riley to ride his horse in and out of the hotel office—an
occurrence that still rankled. “Uncle” Peter flew off the handle, so to speak,
and spluttered, “It’s no-sicha-na-thing! I never permitted that lousy drunken
pie-stealing galoot to ride into my hotel! And just who would pay me for
my hotel if it should burn down? By-GODDIES, you couldn’t do it—Mr.
Bates!”
Since I have quoted Peter Shuemaker detrimental to the character of one
Jim Riley, I shall now explain. Never like to leave any of the old fellows out
on a limb. Then, too, there is still another reason for this elaboration. It is to
keep the record straight. Some, I now learn, are inclined to question if I
have quoted “Uncle” Peter verbatim. That I have you may be sure. I make
no inventions. You can always bank on that. Why, I ask, should I want to
feed you figments of fiction, when memory is stocked with so much of the
real thing—spoken words by the old fellows, a thousand times better than
anything an antiquated mind could conjure up now? And then there is
always the little matter of accuracy to be considered. “No-sicha-na-thing”
and “by-goddies” were his exact utterances.
Not to be confused with the Soldier creek Jim Reilly, who built a house in
town on the site where E. W. Thornburrow’s home is now, this Irishman
owned land up in the Capioma neighborhood—a half section north of the
Patrick Hand land. Jim Riley was a substantial farmer and cattleman. He
was not married. Jim bached on the farm—but spent much of his spare time
in Wetmore, always pretty close to the dram shops. He was a periodical
hard drinker. And a prankster of the first order.
But as time went on—and as he prospered—Jim decided that he could
change the baching situation for the better if his sister, whom he had left in
Ireland years before, were here to keep house for him. He made the trip
back to Ireland, but when he got there he learned that his sister was married
and lived in California. He then made a hurried trip to the west coast—and
in due time the sister, with her husband and several little Ketchums, became
members of the Jim Riley household on the farm here. And through the
hand of Fate title to the Riley lands later passed to the Ketchums.
As Bates had said, Jim Riley did ride his horse into Shuemaker’s hotel. And
as “Uncle” Peter had spluttered, Jim did swipe his pies—baked for a big
dance supper. Riley carted them out on the street in a wheelbarrow, and
passed them out to anyone who would take them. But he paid. Jim always
paid. His reputation for doing that was well established. Like the time when
someone went into Rising’s general store and said Jim Riley was out in
front smashing up a consignment of crockery that had just been unloaded
on the high front porch, giving a war-whoop every time as the crocks he
was throwing crashed in the street, Don Rising said, “Let him have his fun.
He’ll pay.”
Also, Jim Riley did deliberately back his wagon up to the post supporting
Shuemaker’s prized birdhouse, hurriedly threw a logchain around the post
—and drove off, giving one of his famous war-whoops. “Jim’s on another
bender,” the oldtimers said—but I knew he was just plain drunk.
Jim Riley dearly loved to torment Peter Shuemaker. And he liked to play
hide-and-seek with the town marshal. But most of all, Jim loved his drink.
And it was while burdened with a mixture of the two that he met his death
— in 1887. While making a hurried getaway from the marshal his team of
mules, under lash, turned a street corner too quickly, threw Jim out his
spring-wagon—and broke his neck.
And that bird-house—it was a three-decker, about a yard square, with
entrances on all four sides, perched on top of a 10-foot post out in front of
the hotel. Here the martins of that day nested and multiplied in such
numbers as to greatly overcrowd their living quarters. In the late summer
months the new broods would have to take to the roof.
Jim’s log chain, applied at the height of the nesting season, broke up all too
many bird-nests to suit “Uncle” Peter—and it just about caused his to lose
his religion. “Uncle” Peter took his newly-found religion seriously enough,
but when suddenly angered he was a mite forgetful. Lapsing back into pre-
conversion times, his overworked byword—by-goddies—was shortened up
a bit, and with it went a blast of other sulphurous words telling the world
what he meant to do to that scoundrel when and if he could ever lay hands
on him.
Peter Shuemaker was practically the sole support of the Baptist Church here
for a time, in the old days. The Church membership was poor, and there
came a lean time when the members wanted to close up shop—but “Uncle”
Peter said no, “By-goddies,” he’d pay the preacher himself.
Having lost his wife, Shuemaker, in his late eighties, and always a bit on the
contrary side, was now, with descendents in his home, a little hard to get
along with. But he hit it off fine with his preacher. Then, one Sunday
morning, when a beautiful camaraderie between preacher and parishioner
was running high, the Reverend announced something special, a surprise,
for the evening services. That surprise proved to be “Uncle” Peter going
shakily down the aisle, altarward, with a feeble old woman, an octogenarian
from God only knew where, clinging to his arm. She was an “importation.”
Thus, one perceives, that in casting his bread upon the waters it had indeed
been returned to “Uncle” Peter manifold. And for his descendents, who
were keeping a watchful eye on his modest savings, it was as a devastating
bombshell topping a most disturbing surprise. Son-in-law Don Rising
“swore” the old gentleman had been “sold down the river.”
The marriage did not endure.
But, at that, “Uncle” Peter fared better, spiritually, “than did the preacher
who showed him the way. The Reverend George Graham, evangelist, had
pitched his gospel tent on the triangular spot of vacant ground across the
street east of the Catholic Church in Wetmore back in the middle 80’s. With
him was a buxom woman, with rosy cheeks — who sang quite well. And
what with her good singing and George’s impassioned pleas for repentance
they garnered a good harvest—very good, indeed.
The Reverend Graham invoked, with the wrath of Jehovah of old, all the
terrors of hell upon unbelievers. Together, they slew the sinners. Even some
quite good people were swayed into the belief that they ought to make
amends and strive to measure up to the high plane of this super exhorter—
and thus make sure of following through to the Great Beyond. There were
among them converts with Methodist leanings, and converts with Baptist
leanings — even one young lady was possessed of the gift of tongues.
When it was all over here, the converts went their several ways, as the
preacher had advised—or rather they began to map a course by which they
might make the takeoff for the long journey. Then, with the second stand
away from here — somewhere down around Lawrence — the preacher and
the lady were publicly exposed for unholy conduct.
And yea, verily, the Reverend had a family somewhere abroad in the land.
Repercussions hit hard back here. The one great wrong done our converts
was, as you might expect, heaped upon them by the unbelievers who had
been consigned to the everlasting fire of brimstone by the now fallen
preacher. As is usual with emotionally recruited converts there was some
immediate backsliding, or cooling off, but when “twitted”—that’s what they
called it then—by the ungodly, the stampede back to normal got under way
and was, in the days that followed, made complete—save one. “Uncle”
Peter was seemingly the only one of the many who could bring himself to
believe that religion was religion—something pure, and worth keeping,
even though it had been delivered to him through the channels of a dirty
carrier.
There is an old saying that “one should give the devil his due.” I’m sure
that, regardless, the magnetic George did a power of good in his revivals
here. While, it is true, his converts did not choose to “join-up” after the
crash, until the backwash of that scandal had become tempered by time,
they did, however, accept the opportunity to come into the fold under
another standard bearer. And, unfortunately for the Baptists, the Methodists
were first to hold a revival—and reap the harvest. And the girl who was
“called” upon to babble in tongues, gave up the pursuit when it was evident
that she was fooling no one but herself.
At the time of the exposure, I was temporarily working for Bill Granger on
his Centralia Journal, and boarding at the old McCubbin House, down by
the tracks. Ed Murray — later, Mo. Pacific agent in Wetmore for many
years—was clerk at the hotel. Professor Roberts, principal of the Centralia
Public Schools, was the third person present when the Evening Daily
newspaper was brought in. After reading the exposure article, I passed the
paper to Mr. Roberts, with comment that I had attended Graham’s revival
meetings in Wetmore. Mr. Murray had his say about preachers in general,
and about one Reverend Locke in particular—of the latter, quite
complimentary, however.
As he read, Mr. Roberts said, “Say—you, a newspaperman—here’s
something you ought to commit, for future use.” For future use? He meant,
let us hope, only as a model for phrase building to be used on occasion.
That Mr. Roberts, he was a mighty clever young man—quite young, then. It
was a long time ago, sixty-one years to be exact — but I still remember.
The newspaper report was vague as to the exact nature of the preacher’s
misstep, and I shall not attempt to state it here lest I might do someone an
injustice. So, then, let’s let George do it. The paper quoted him, thus:
“I have the consolation, small though it be, of knowing that though my bark
goes down amid the turbid waters of Illicit love the shores of Time are
marked with many such wrecks.”
Prettily phrased. But no further comment.
NOTE — This is okayed, “No-sicha-na-thing.” “By-Goddies,” and all, by
Hettie Shuemaker-Kroulik, (70), granddaughter; and by Peter Cassity, (80),
grandson. And they go further, saying: The $1,000 he paid to rid himself of
the woman, plus what it had cost him to get her (preacher’s reward) just
about cleaned “Uncle” Peter. And Cassity says the pies swiped by Riley
numbered exactly forty. Jim paid double, as always—and liked it.
And now wouldn’t it be nice if I could say here that Cassity was one of
those converts? I’d say it, anyway—if I weren’t afraid Peter would tell on
me.
MY BEST INVESTMENT
Not Hitherto Published — 1947
By John T. Bristow
Girls — Girls — Girls
After mulling the old thing over, I know now that the boy who sat with me
in the reserved section at Evangelist George Graham’s meetings, as
intimated in the foregoing article, was not Peter Cassity. It was his brother
Bill. Pete tells me that he was farming at the time over on Wolfley creek
and did not attend the meetings regular—but don’t ever think Pete did not
remember his raising, when he did get in.
Bill Cassity had the nerve and the Biblical knowledge to stand up in a big
way for his Maker. That boy had an almost irresistible line, and it was, at
times, questionable whether the minister, or the converts—with Bill well
out in the lead — were doing most in the matter of gathering in the
prospects.
When my uncle, the Rev. Thomas S. Cullom, minister of a Methodist
Church in Nashville, Tennessee, with his wife Irene, and two daughters,
Lora and Clevie, paid a visit to their Wetmore relatives in 1908, the
Reverend told me that in his Church, and throughout the south, it was
customary during revivals to have “exhorters” stationed in the congregation
to give supplementary support to the minister’s pleas for the redemption of
lukewarm and tottering souls.
I asked him if his exhorters ever broke in on his impassioned pleas in a
discordant manner—that is, a little off key? “Cert’nly,” he said, with fine
southern accent. “My exhorters are very devout workers for the Lord, and
sometimes when filled to overflowing with the Holy Ghost, they say their
lines and then keep right on exhorting and sometimes steal the whole
show.” This ungodly reference to his Church as a show was made with a
wink and a grin.
And so, with the old time revivals here, the minister’s exhorters, under
another name of course, sometimes ran away with the show. This brings us
back to Bill Cassity, first born of Newton and Anne Shuemaker-Cassity. Bill
did just that on at least two occasions in the Evangelist’s revival here. He
had the Christian training to do it courageously.
While still a young man, Bill Cassity went to Colorado, worked in the
mines and smelters, at high wages, and ordered the Spectator sent to him
there — and later to Los Angeles. Bill came home once, told me he liked
his work in Colorado, or rather the big wages—but he did not like the
characters he had to associate with. In California, still on the right side of
the laws of God and man, Bill pushed his penchant for righteousness a little
too far for his own good. As a detective, self-appointed or otherwise, he
learned much of the ways of the Los Angeles underworld—and, it was said,
the boys took him for a ride and failed to bring him back.
And again, some twenty-odd years ago, Than Gustafson, a former Wetmore
man, older brother of our Fred Gustafson — and in a legal way Fred’s
brother was also his brother-in-law, the two Gustafson boys having married
sisters, Adelia and Ophelia, daughters of S. M. Hawkins—is supposed to
have been taken for a one-way ride by the Rocky Mountain crooks. He left
his home in Denver, a wife and two children, one evening in line of his
duties — and was never heard of again. Than Gustafson evidently knew too
much for his own good.
When in gangdom, it is wise to be dumb.
Under the old system, in revivals, the first converts either appointed
themselves or were delegated to work among the congregation as boosters
for the minister—something like Uncle Tom’s “exhorters.” They would go
out in the audience, usually in pairs, and plead with you, cry, and sniffle
over you—an actual fact—in a manner that would - make you feel mighty
cheap. The boy who respected them, loved them through long associations,
was struck dumb.
One particularly sanctified woman—no one could ever doubt her sincerity;
I had known her for years, and she was always so—with redoubled sniffling
tendencies as of the moment, accompanied by the prettiest girl that ever
walked down a church aisle or any other avenue in Wetmore, a girl whom I
had just about given up as lost to a certain rich man’s son, on account of her
papa’s preference for the other boy, and because “papa” said I played poker,
made a firm stand in front of me one night. I knew before the old girl began
to sniffle that, on account of the young girl, I would, sooner or later, find
myself in a front row. More than one boy went forward in that meeting
because he did not have the heart to disappoint them—and maybe there was
also the attraction of a girl. Girls were more susceptible to the worker’s
pleas.
The older woman talked rapidly, between sniffles, in terms only partly
understood by me—but the girl’s radiant smile told me much. I would not
permit them to march me up to the front, as other workers were doing with
prospects, but I promised to sit with the young girl in the reserved corner on
the following night—and see what would happen.
I hope the good people will pardon me for mixing my worldly activities
with the more decent church sittings — but this seems the opportune time
for me to ‘fess up. In this story I mean to come clean—tell everything, and
have as little of the old hero stuff in it as is consistent with the making of a
good story.
I had been to church—Methodist protracted meeting — and then dropped in
on the boys in the DeForest store at the virtual close of a little poker game.
Even now I hate to think what Henry DeForest would have done to us had
he known his dry goods counter was serving as a poker table. One man,
Willard Lynch, dropped out while the deal was in progress, and said I might
play his hand.
This was to be my first poker game. Also, it should have been my last—but
it wasn’t. Not that it ever became an obsession with me. But, in general, it is
not an elevating attainment—and it is something which any self-respecting
young man can very well do without. It was, however, my last game in Mr.
Henry’s store. I wanted to retain, at all costs, his respectful opinion of me.
And the other boys finally saw the error of their ways — and changed their
meeting place. On the cleaner side, I will say that I never learned to shoot
craps, never bet on elections, ball games, or the horses; never drank or
caroused, wouldn’t feel “at “home” at the popular cocktail party; was never
in court as complainant or defendant—and was only once in my whole life
in court as a witness, at which time, had I told the Whole Truth as I was
sworn to do, I could have been jailed for my ignorance. I was an untutored
member of the Kansas Grain Dealers Association, which was under
investigation. Also, I want to say in the outset that this poker stigma was not
the thing which had lowered me in the opinion of “Papa.” It was the more
powerful evil—money—of which I had none. But there was one bright spot
in the clouded picture. The rich man’s son looked a lot better to “Papa” than
he did to the girl.
Well, in this, my first poker game, I picked up four natural aces, and if you
know only as much as I knew then, you would consider it a top hand. No
one had told me they were playing the joker wild, “cut and slash.” I bet a
nickel. Alfred Anderson called, and raised me a dime. Two of the other boys
called Alfred’s fifteen-cent bet—and the dealer, Sidney Loop, (clerk in the
store), dropped out of the play. I thought my four aces were good for ten
cents more, and not possessing a loose dime, I dug up a five-dollar bill.
Alfred was up on his toes, and said, “You aiming to bet all that?” I replied,
“No—only aiming to call your dime raise.” Still upon his toes, a little
higher now, he said rather anxiously, “If you want to bet it all, I’ll call it—
you can’t bluff me.” I took one more look at my hand—and not one of the
aces had gotten away. And then I said, “All right, I’ll just bet it all.”
Now, if you know the game, you are maybe expecting to hear that he had a
set of fives, including the joker of course. But it was not Alfred who held
them. His four kings were not good. It was the dealer, the man who had
dropped out because I had dropped in, who had five fives.
But this I did not know until two days later, not until after I had gone to
church again and contributed $5.00 to Mrs. Draper’s fund for buying
Christmas candies for her Sunday School kiddies. Alfred’s sister Phoeba, as
personal representative of our dear old Sunday School Superintendent, took
my contribution with gracious acknowledgment, as though it were not
tainted money. And Mrs. Draper—the less chivalrous boys called her
“Mother Corkscrew” because she wore her gray hair in ringlets at shoulder
length—came to me on the double quick, shrieking her praise of me, and
intimated that this generous gift might get me places.
Alfred said that inasmuch as he surmised he had been cold-decked out of
the five—thankfully with no aspersion attachment—that I should have at
least given the donation in both our names. But that would have been risky.
Alfred was a rather white “black sheep” in a very religious family, and Sis
would most likely have wanted to know how come? The fact that Sidney
and Willard were keeping company with sisters at that time may have had
nothing to do with the introduction of that cold deck. And then again it
might have. Sidney said the fellow needed “taking down” a bit — and that
it was planned to give the losers back their money. A fat chance they would
have of getting their money back now.
Until now I had only stood, by and watched a penny-ante game in the new
opera house over the Morris store, where the clerks — Dave Clements, Bill
McKibbon, George and Chuck Cawood, Bob Graham—and some younger
fry, congregated on Sundays. And then, too, as a kid, I had been present on
several occasions at a somewhat bigger game in the Neville residence on
this same corner. But here I did not have a chance to closely observe the
technique of the game—for I was under the table most of the time. The men
played altogether then with “shinplaster” money — undersized ten, twenty-
five, and fifty cent pieces of U. S. paper currency, and the breeze caused
from shuffling the cards would sometimes blow the money off the table.
Mr. Jim Neville said I might keep all I could get my hands on — and I think
it was a sort of house rule that the players were not to contend roughly with
me for the fluttering pieces. Still I think I got more kicks than the law
allowed.
Also, I once saw the women playing poker in this same home—and they
were using “shinplaster” too—but they were not generous enough to invite
me to go down under. I do not wish to name them. Nor would I have
mentioned the boys’ names but for the fact all of them have now gone to
their reward. And, besides, despite the undercurrent that it was not
considered strictly genteel, everybody, more or less, played poker then—
even, it was said, Father Bagley, our first High Priest, would take a hand
occasionally. There was a regular fellow. For him it was Mass of a Sunday
morning, then base ball or horse-racing in the afternoon, without fail.
With this slow and awkward beginning it was a long, long time before I got
nerve enough to sit in a private poker game as guest of a friend, in Kansas
City, with a player who afterwards became President of the United States.
He did not impress me as likely timber then. But, may I say, that when once
in the running, he showed ‘em that he was truly from Missouri—and that,
surprisingly, he could, in a pinch, run like a scared rabbit. Politics was his
forte.
In explanation of the Girl-Papa-Richboy incident: I had sent a boy with a
note asking the girl for her company for a dance, a private dance to be given
by our select crowd, of which she was a favorite. The boy came back
without a written reply—but he said she told him to tell me that she would
go with me. This being rather unusual, I asked the -boy if that was all she
said? “Well,” he said, “her mother said, ‘Now, girlie, you know what your
father will say’ — and the girl said, ‘I don’t care, I’m going with him
anyway’.” I had not known about the rich man’s son trying to edge in, and
this indicated slap by her papa was a grievous blow to my ego.
I sent the girl another note, telling her in simple words—I always made ‘em
simple now since having once, to no avail, slopped over ridiculously — that
I had wormed out of the boy the remarks between mother and daughter, and
that in consequence thereof I deemed it wise for me to cancel the date, until
I could find out what it was all about. I may say I never sent but one
formally phrased note to a girl in all my life—and that got me exactly
nothing. That literary boy, Ecky Hamel, dictated it for me, and to make
matters worse, it was to his girl. And he really wanted it to click—to ward
off, in his absence, some dangerous competition.
However, I once got a neatly written acceptance to an ultra-formal and
gorgeously phrased note bearing my name, which I didn’t write. I was a
new boy in Seneca at the time. I met a lot of girls at the skating rink in the
old Armory building on upper Main Street. Ena Burbery, pretty and
agreeably alert, was good on roller skates. Ena and four other girls worked
as trimmers in the millinery department of the Cohen store. Ena talked. And
the girls, all but one, joined in mailing her a note bearing my forged
signature requesting her company for a swank party three days hence. Ella
Murphy, one of the five, boarded and roomed at the Theodore Wolfley
home, same as I did while working on Wolfley’s newspaper, The Tribune.
Ella said the note was formal and softly silly, and so did Ena say it was
awful — but, she giggled, “I was not going to let that spoil a date,
especially for a party like that.” Now, the ridiculous part of it all is, that it
was an exclusive party to be given by Seneca’s upper crust, to which I had
no invitation. But, even so, it gave me elevated status for a little while, in a
limited way. We compromised on the rink. And the girls, whom I never did
meet, sent me an apology, through Ella Murphy, for recklessly abusing my
name—and getting the girl a date. Ena was the section foreman’s daughter,
but that was no handicap. I myself married a section foreman’s daughter,
picked her for a winner from a sizable field of promising prospects.
Naturally, I wanted to know more about the status of the rich man’s son—
and I got it too, back at the gospel tent the next night. The girl said nothing
at all about my poker-playing proclivities. She was too sensible to try to
reform a boy. Her idea was to pick ‘em as suited her fancy—and trust to
luck. Indeed, she said in rebuttal of her father’s expressed opinion of me,
that if her mamma only could have kept her mouth shut everything would
have been all right, and that I would have never known. “And besides,” she
said, “You don’t drink, and papa does—a little; and you don’t smoke, and
papa does, though he does not smoke cigarettes.” A cigarette smoker in
those days was considered cheap. How times have changed. The girl had
overlooked one of “Papa’s” weaknesses, but for me to have mentioned it to
her then would have got me nothing that I was not now likely to get
anyway.
This exchange of ideas took place in the reserved corner of the arena in
advance of the regular session while other congregated young people were
likely thinking of an afar off haven having streets paved with jasper and
gold. Something about streets and jasper and gold ran in the lines of the old
song books. Also, I dare say, some of the converts might have cringed a
little at the thought of an everlasting fire of brimstone—this idea emanating
from George, the Evangelist—which the wayward and lukewarm alike
might, if they didn’t watch out, fall into in a last-minute rush for that afar
off haven.
Every evening during his meetings Reverend Graham would institute a two-
minute session of silent prayer. In - view of George’s admitted downfall at a
later stand, I trust it will not now be considered sacrilegious for me to
hazard an opinion that those silent periods offered the preacher an excellent
opportunity to pray for grace.
It was not required by custom then for those seeking salvation to come clear
down to earth, and some merely bowed their heads, rested them on the
backs of deserted chairs, and whispered when so inclined. The girl and I, we
did not desecrate the hallowed moment. We didn’t have to. Silence was
golden. I was conceited enough just then to believe that this beautiful girl,
thoroughly repentant or no, would have gone through George’s pictured
purgatory for me.
And nothing happened that could be chalked up as material gain for the
better life. Well, I ask you, how in the name of high heaven, could it? I’m
not particularly proud of it, though. But, you know, if your chariot does not
come along, you can’t take a ride. I certainly do not wish to cast reflection
on the Church. The Church, as a Church, is really a grand institution. I
should hate to think where we would be in a world without it. Henry
DeForest, Yale graduate, said the tent doings was proselytizing.
Perhaps you would like to know how I fared in the days to come with this
renewed lease on life which the Evangelist’s revival had brought me? Well,
“Papa” shelved his dislike of my poker-playing, and both he and “mama”
greeted me as a friend ever after. They were really fine people—I might say
the very BEST, with capitals.
“Papa” had played a little poker himself—and that too, by-gosh, in our
penny-ante game—and his wish for a switch in the matter of his daughter’s
company was based on too slim premise to set store by, now that the girl
had told him with flat-footed finality that it would not work.
And the girl? Well, I had to go away, first to Centralia, then to Seneca to
help Theodore Wolfley print his newly purchased Tribune, and I turned her
over to my best poker-playing friend to keep for me against the time when I
might return.
Now, to do me this small favor my friend had to drop another girl with
whom he had been keeping company steadily for two years. He probably
saw possibilities in the change, but he was really too fine—and too ably
assisted by the girl—to take advantage of a friend’s absence.
As my trusted friend and my girl in escrow were already lined up for the
party that first night after my return, it was mutually agreed that—just for
once—I should line up with my friend’s discarded girl, who was still free. It
worked out all right—and it was wonderful to be back with the old crowd
again.
Now, don’t jump at conclusions. Though she was a mighty fine girl, and
good looking too, I did not find her preferable to the other girl. Just why I
made it a regular habit for nearly a year, was quite a different matter.
We all belonged to an exclusive clique known as The Silver Stockings. Why
so named I never learned. One unalterable requirement for the men was that
each had to bring a girl—or a wife. No “stags” were permitted at our
parties. This was because a certain unwanted young man had the disturbing
habit of sneaking in at public gatherings and monopolizing our girls.
The thoughtful young man of that period did not think of marriage the first
time he went out with a girl. In our community none but the rich man’s four
sons were financially (in prospect) able to indulge in such dreams. And,
besides, by this time I had had a change of heart—resolved to consider the
future of the girl. After all “Papa” might have had the right idea. I figured
that an attractive girl like she, would not be justified in playing along with
me until I could make my stake.
And again, were I to pursue my chances—which at this time were, I
flattered myself, in a high bracket—who could say with certainty that
“Papa” would not someday become afflicted with a recurrent attack of that
silly notion the first time that the favored son, or maybe another of the
RM’s sons might strut his stuff in the presence of the girl. Then, too,
something fine—alas, something very fine, was now gone out of the picture
that could never be returned. I reluctantly decided to let matters drift along
as temporarily planned the first night back home—and see what would
happen. It was my hardest decision.
I had seen too many people trying to make a stake and raise a family at the
same time. My father made more money than most—but with ten children,
it was slavery for him. He worked sixteen hours a day at his trade as
shoemaker—and even then he had to skimp, and work and skimp. But he
took a philosophical view of matters, and on the whole his was a rather
contented life. One time when he was complaining about the difficulty of
getting ahead, I suggested that maybe he had erred in first taking on the
responsibility of raising a big family.
He said, “Well, they kept coming and I couldn’t knock ‘em in the head.”
I said, “They didn’t start coming until after you were married—”
He yelped, as if something had stung him, “Of course not, you young
upstart!” That was a time when he would have been justified in applying the
kneestrap, his ever ready implement of correction, to my posterior. But my
father was a forbearing man.
I said, “Gosh, Dad—I only meant to say if you had waited until after you
had made your stake, you would not now be bothered with this burdensome
load.”
He said, quickly, “If I had waited longer where do you think you’d be now,
young man?”
Well, that was something to think about. It might have upset the whole
continuity. I think we older boys reminded him too often of the excess
baggage he was struggling along with—only, however, when he would
begin his lamenting, usually about the high tariff.
I can think of nothing more disturbing than to be caught short-handed
(otherwise broke) in a community marked by a dearth of opportunity to
earn a living—-With dependents to care for. Such was our country in the
early days. My parents had rubbed up against this situation on numerous
occasions. However, unlike some of our neighbors, the time never came
when we did not have enough to eat. But that “hand to mouth” rule of living
could not rub out the anxiety.
It was an era when the ambitious young fellow was of necessity compelled
early in life to begin laying-by for the “rainy day” if he did not wish to run
the risk of becoming an object of charity—and who did in the old days? It
was then considered about the last straw. It took a long time to lay-by a
competence in the old days. The average wage-earner gets as much per hour
now as was paid for a whole day’s work then—when ten hours was a day.
This is not to say the young “sprout” could not marry before he had a
competence. He did—recklessly. And paid the price.
It was to avoid such conditions as this that I made a firm resolve to defer
marriage until I could make a stake.
I set my goal at $10,000, and when things got going good I kept right on
going until this goal was more than doubled — and in subsequent years
learned that it was none too much:
However, in strict honesty, I think this cautious streak was inherited rather
than instilled in me by observations. My father had entertained the same
cautious notions. Orphaned early in life, he made his own way—saved, and
had what he called a nice nest-egg at the age of 25. He went from Kentucky
over into Tennessee to visit relatives, met my mother while there—and
married her the next time he came into her back-woods community. And
had it not been for the cruel Civil War—and the guerillas—I am pretty sure:
that I would have had a rich Dad regardless of his super-abundance of kids.
However, conditions changed for the better for father. When his boys got
big enough to lessen the burden, and then in time lift it altogether, he had an
easy life. My brother Frank worked with him in the shoeshop, and at the
same time conducted a shoe store in the front end of the building, with our
sister Nannie in charge. When Frank decided to go to California to join his
brother Dave in business, he gave them the shoe stock. I had written
insurance in the sum of $1,000 for Frank, and when the assigned policy was
about to expire I mentioned the matter one day at the dinner table. Father
said, “Oh, I don’t need any insurance.”
I renewed the policy anyway, paid the premium myself, and said no more
about it. Then, some months later, a fire destroyed the old Logue frame
store building across the street, in early evening—and the town was out in
numbers. There was little chance of the blaze reaching my father’s shop, but
he and several excited volunteers were making ready to remove the shoe
stock to the street. I told him that he better just get his books and records
where he could put his hands on them in case of need, and to leave the stock
in the building for a while, at least. Thinking to ease his fears, I said,
“You’ve got a thousand dollar insurance policy on the stock.” He
exclaimed, excitedly, “Oh, that’s not enough!”
By this time—we are now back again on the matter of girls, mostly — the
girl’s papa had been elevated to the Mayorality, and the family was now
operating the Wetmore hotel. On one of my trips home from Seneca, after
spending a pleasant hour with the girl, I dropped in on the poker game, just
to greet the boys, and watch the play. I had reformed then — mostly, I
think, on account of the girl. Incidentally, I may say I reformed more times
than a backslider ever confessed his sins—every time, I think, on account of
a girl—before finally realizing that it was not the way to build character.
The game then was in the Billy Buzan residence—af ter his wife’s death—
on the corner where Bob Cress’ residence is now, west of the telephone
office. It was the original William Cawood location, with the west portion
of the high fence (seven-foot up and down pine boards) still standing. That
high fence had enclosed four lots, and held in captivity a “pet” deer for
several years. When the Mayor and a guest of the hotel came in at the front
door, I slipped out the back door, as I thought unobserved by His Honor,
and streaked it, in bright moonlight, to the fence and went over almost
without touching. The next day the Mayor said to me, “Young fellow, I saw
your shirt-tail going over that high board fence last night.” But he hadn’t. It
was before the young sports had begun to wear their shirt-tails on the
outside of their pants. And then again I never was guilty of that slovenly
habit.
About that deer. It finally jumped over the gate at the southeast corner of
the enclosed grounds—and was gone for several days. But it came back and
jumped in again. Then, it made a game of jumping out and jumping in —
with periodic trips to the country. Then, one morning there were two deer in
the enclosure. I think the “pet” deer tried its best to domesticate the visitor
— but after three days, the call of the wilds claimed them both.
Some years later—after he had spent a couple of years in Arkansas, and was
now back in the hotel again, in Wetmore—”Papa” was in a tight spot at
Enid, Oklahoma, the third day after the opening of the Cherokee Strip,
September 16,1893. He had made the run, staked a claim, and was in line—
a very long line—at the Land Office, waiting his turn to file. I had already
filed on my claim. While in line, I observed soldiers, who were supposed to
be on hand to see that everyone would get a fair deal, were running in
people ahead of me—and a little later, a man I shall simply call Eddie—
apparently in the role of chief grafter—whom I had known in Wetmore,
approached me with a proposition to advance me in line for $5. I was too
near the door to be interested—and besides, my brother Dave who held a
filing number next to mine, promised to “wipe the earth up” with Ed if we
should be delayed further. Might say here that the gang followed this
remunerative activity with another dirty practice. They filed contests on
claims, so that the rightful locators would, in many instances, buy them off
rather than stand the expense of fighting the case. Then Dave had to give
Mr. Ed that promised thrashing. It got Dave a prompt withdrawal of the
contest. I was the only one of our party of four who did not have to fight a
contest. My friendship, or co-operation with the crooks, whichever way you
choose to look at it, had, I presume, saved me.
After I had filed on my claim, I carried the “good” news of Mr. Eddie’s
activities to “Papa.” I knew he was anxious to get back home to his hotel
business, where he was trying hard to re-establish himself after returning
from Arkansas. He asked me to contact Mr. Eddie for him—and said, “I’ll
be your uncle.”
The soldiers advanced him to near the door—and there the line became
static once more, as other advancements were being pushed in ahead of
him. Then Ed told me that for $10 more the soldiers would put him through
the door without delay. “Papa” dug up the $10, and said, “Do this for me
Son, and I’ll dance at your wedding.” Now he could call me “Son” and
offer to dance at my wedding.
There are three girls prominently featured in this story, whose names I do
not wish to divulge. Substituting, I maybe should call the first one Miss
Beautiful, for she was all that. But from here on, until further notice, I shall
refer to them as My Best Girl, The Old Girl, and The Kid.
In all too short time my nemesis, in the person of a certain rich man’s son,
an older brother of that other boy, got on my trail. I do not think it was to
avenge his disappointed brother, but it could have been that. He told the
boys it was to prove that he was “man enough” to “bump” me.
Well, just for once, it was not a bad guess. He would be working on fertile
ground. I didn’t care too much for the Old Girl anyway. She was my senior
by four or five years, and naturally she would welcome a good “catch.” It
was understood between us that she was only filling a vacancy, and thereby
providing a way to keep us in the Silver Stocking circle. The thing I didn’t
like was to be “bumped” just for the fun of it, as viewed by the RM’s son.
Mike Norton, clerk in the DeForest store, saw the rich man’s son write a
letter to the Old Girl, and he thought this would be the time when the RM’s
son would try to make good his boast. Three days hence there was to be a
picnic in a grove south of Netawaka, and the Silver Stocking boys and girls
were lining up to go in a body. Mike and other members of the circle put in
two hours looking for me. The boys, and the girls too, were all for me, in
this instance — but not even the King’s Horses could have stopped that boy
in his purpose. The postmaster showed me the letter with the OG’s name
spelled out in bold relief—and I was off at once, thinking I would now
show this RM’s son that he could not do this to me.
The Old Girl said she was awfully sorry—that she had promised another,
naming the rich man’s son. I said, in substance—though really not sore at
the OG, I think I was not in a frame of mind to phrase it just so—”Let’s see
where we stand. The way things are shaped up now, I’m out—that is, barred
from the Silver Stocking crowd by the rules of my own helpful making.”
She suggested that I go back to the girl I have designated as My Best Girl—
said, “I KNOW you can, if you will just spunk up a little.” I had never
“spunked” much with the OG.
“But,” I said, “if I should succeed in dating her, someone else would be out,
and that someone is your old beau. Likely timber maybe. Then, in case your
date does not choose to repeat, you might still have a chance to get back
with the old crowd.”
She laughed — the OG was feeling pretty good, just then—and said, “I
hadn’t thought of it that way.” Now she giggled, “But, you know, I could
always be a hanger-on, maybe even go with you and your girl—just in
case.” A boy was permitted to take more than one girl—even a flock of
them if he were unlucky enough.
Now the atmosphere around the OG’s home had changed, with exultant
spirits taking a nose-dive. That letter was for the purpose of calling off a
date. She was really too nice a girl to be buffed around like that — but
please note that I did not hold with any such buffings. She had forfeited her
chance to go with the crowd to the picnic. Now, more than ever, she wanted
to go. She first took her troubles to her bosom friend, Bessie Campfield,
wife of Judge Elwin Campfield. She wanted to know how could she, with
propriety, get word to me that after all she would be free to go with me to
the picnic. Bessie had spent some anxious moments trying to round up a
courier to apprise me of that letter. She said to the OG, “I don’t know about
that now. I could have told you about that fellow’s egotistical designs.”
The Old Girl lived with her aged parents, and when they would go away for
the night, as they often did to visit another daughter in the country, she
would have a young neighbor girl—not too young, but much younger than
she-stay the night with her. The old folks were away now, and the young
girl had been called in for the night.
The Old Girl was still worried. I’m now almost sorry that I ever started this
“Old Girl” differential, as it smacks of disrespect — and I do not want the
reader to form any such ideas. The OG first asked the young girl to come up
town with her—then, remembering that her best friend had dropped a hint
that the ground upon which she now stood was insecure, she decided that
she was not constitutionally able to face me just then with her problem. She
sent the young girl, alone.
But the Kid—that’s what they called her when we went together to the
picnic, and thereafter as a member of the Silver Stocking crowd—said, “If
you go with her now, you will be the biggest fool in the world. All she
wants to go with you for, is to see who he takes,” naming the RM’s son.
The Kid was smart.
But please do not think the so-called Kid was betraying a trust. She was
really a woman now. And, besides, she had reason to believe that, to use a
homely expression, she were very soon going to get the OG’s goat, anyway.
And moreover, the Old Girl later told the “Kid,” perhaps in a gesture of
discouragement, that I had gone with her steadily for nearly a year, and had
never tried to kiss her. Had that not been the truth it would have been libel. -
In the old days, the prudent young man did not dare kiss an old girl who
was only filling a vacancy.
Prior to this, the “Kid” and I had “starred” in a local entertainment entitled
“Beauty and Beelzebub” — and mutual admiration had blossomed then.
She was the Angel and I was the Devil. In the tableau, the Devil, encased in
a tight-fitting black sateen cover-all, with horns and a four-foot forked tail,
was suspended on wires about four feet off the floor when the curtain went
up. Then the Angel, up in the clouds, began the descent with song, the
singing increasing in volume as she came down bare feet first, with
outstretched wings, settling in front of the Devil. The “Kid” made a pretty
picture, with her abundant dark hair — which, I happen to know, came
down nearly to her ankles — spread over the white flowing covering whose
traditional folds parted in front just enough to indicate that she dwelt in a
place where shoes and stockings were taboo. The Angel departed by the
same route—wire and windlass mechanism—went up into the clouds from
whence she had come, with more singing, at first in full voice, then fading,
fading, fading away in a manner denoting distance. In her young budding
womanhood the “Kid” made a beautiful Angel — and the clear, sweet
singing was out of this world.
Coral Hutchison was at first considered for the Angel. She was a beautiful
girl, and a beautiful singer—and while she had a wonderful head of hair,
quite as long as the “Kid’s,” its rather too blonde shade ruled her out. So the
“Kid,” with the requisite dark hair, was given a place in the spot-light—and
Coral did the singing behind the scenes.
Sorry, I can’t tell you what event or setting that tableau portrayed. There
was much more to the show, speaking parts and superb acting. And though
clearly the “Kid” and I were “it,” the whole show was titled “Beauty and
Beelzebub.”
At the picnic, my adversary, the rich man’s son, said to me, “I see you’ve
got a new girl. How come?” I said, “Yeah—likewise you. Thanks for the
assist.” After I had started to walk on, he called, “Hey, John, whatsha mean
by that?”
He was with Lou Kern. Hattie and Lou Kern, and Nina and Emma Bolman,
were four Netawaka girls that were popular with our Silver Stocking crowd;
as were also Caroline Emery, living in the country northeast of Wetmore,
and her visiting friend, Mamie Blakeslee, a former neighbor whose home
was now in Savannah, Mo.
Mamie Blakeslee was a strikingly pretty girl.
I shall now dwell a bit on a personal incident in connection with this
beautiful girl. It was away back in 1884. I don’t think the girl was on my
mind that day when I went to St. Joe. But, in St. Joe, I ran onto Bill
(Hickorynut) Bradley who was on his way to Savannah, and he asked me to
go along with him. One Oliver Bateman was to be hanged for the murder of
two little girls who had caught him in an embarrassing act. The railroad was
offering excursion rates, and the sleepy old Missouri town was decked out
in celebration colors, with refreshment stands all along the lane from the jail
to the gallows in an amphitheater in the nearby woods—everybody on the
make.
Unlike Hickorynut, the hanging did not interest me, but the thought of
seeing Mamie did. I called at the Blakeslee home on the outskirts of
Savannah — it was a farm traded by G. N. Paige for the Blakeslee farm
near Wetmore—on the pretense of wanting to see Mamie’s brother Edwin,
who had been my schoolmate in Wetmore. He was not at home. I remained
a reasonable time with Mamie, aiming to work up a little courage, and
maybe ask her to go places with me—but lost my nerve.
Two hours later I met Mamie, with another girl, on a downtown street near
the St. Charles hotel. Mamie said there was to be skating at the rink that
night, and would I like to go? I certainly would. So now, after all, we would
be going places together.
I called at the Blakeslee home for the two girls, and the ‘skating was going
fine. Then, of a sudden, Miss West told me that Mamie was in a jam. Her
steady, a traveling salesman, had unexpectedly dropped in on her — and,
for some reason, likely well founded, Mamie had not intended to let him
know about her going out with another fellow.
I told Miss West that we could fix that all right, if she herself did not have a
steady sticking around somewhere. Miss West laughed, and assured me she
did not have a steady. “If agreeable,” I said, “you shall now be my
company, and, to all appearances, Mamie shall be the hanger-on, free to
desert me for her steady.” Miss West laughed again, though she looked as if
she were a little concerned about my reference to Mamie as the new hanger-
on. Well, it was a slip. It was a term often applied to the extra girls in our
Silver Stocking circle.
While visiting in Wetmore before this, Mamie had gone to a dance in
Netawaka with a local man who proved to be not to her liking, and she had
quit him cold at the dance hall door. Though it would hardly cause a ripple
now, it was then considered about the worst thing that could happen to a
young fellow’s social standing. I do not wish to identify him—yet I must
give him a name to be used in Mamie’s pay-off to me for liberating her at
the Savannah rink.
In the substitution of names, one is liable to innocently hit upon somebody’s
real name, and to avoid the possibility of making this error, I shall give him
the surname of his business partner, and go through the customary formality
of saying that any similarity in names is purely coincidental. The man was
half-owner of the livery stable from which we all got our “rigs” that night.
And, anyway, the partners left here together for the state of Washington
many, many years ago, and there should be no chance for repercussions
now.
Mamie knew that I was familiar with the Netawaka incident—in fact, it was
I who did the shifting with Sidney Loop to get her back home. When Miss
West had delivered my message, Mamie broke away from her steady, rolled
gracefully around the hall, and plumped herself down by my side, saying,
“Thank you so much! It gets me out of an awful jam! And I want you to
know that this is no Dr. Fisher deal!” I wondered? You know a girl, in
competition with other girls, might strive for long to vamp a certain good
catch—which is always a girl’s privilege—and then when the chance offers,
find herself tied up for the time being with someone that right away stinks.
The Blakeslee family formerly lived on a farm four miles northeast of
Wetmore, directly north of the old Ham Lynn farm. Mamie’s father, Nelson
Blakeslee, often called at my father’s shoeshop for a visit. One time they
planned on chartering a car together and shipping to California. I did not
know Mamie then—but have since wondered what might have happened
had they gone through with their plans.
Evidently Mamie did not make the most of the opportunity afforded her that
night back in Savannah. She married Frank Schilling, of Hiawatha. There
were some dark surmises that she stole Caroline Emery’s beau. “Stole” is an
ugly word to be written in connection with this sweet, conscientious girl—
as I knew her then. I would rather believe that Miss Emery’s beau was a
man of rare good judgment. I have not seen Mamie since that night at the
skating rink in Savannah. Now widowed, she lives in Fairview — thirty
minutes away from Wetmore.
Back again on the main theme: In the days which followed, I said to myself
—thought it with vengeance, anyway—that I would like to see the color of
the hair of any d—d RM’s son that could make me give up this one,
meaning the “Kid,” of course. And may I say that for once I now believed I
had my girl matters well in hand.
But, believe it or not, still another son of that same rich man tried his
darndest to edge in. At this time the younger boys had the habit of lining up

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Modern NMR Approaches to the Structure Elucidation of

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MASTERING PFSENSE 2 4 master the art of managing securing

Oxidative stress and redox signalling in Parkinson s

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Universal Approaches to Support Children s Physical and

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Hundred Years of Structure Elucidation 1

Part I Compounds with only Oxygen Functionalities 11

Part II Compounds with Nitrogen and Oxygen Functionalities 95

13 Lysergic Acid 121

Part III Compounds with Additional Functionalities 207

Part IV Compounds without Heteroatom-Functionalities 237

Part V Can You Do it Yourself? 251

It is a well‐accepted standard in the education of scientists to advise the novices

instances, however, the experimental facts have been combined to another,

July 24, 2014 Reinhard W. Hoffmann

Hundred Years of Structure Elucidation

Classical Methods in Structure Elucidation of Natural Products. First Edition, R. W. Hoffmann.

the “structure” of a compound. This framework was provided by Kekulé (1857)

Structure Theory: Stereochemistry:

Of similar importance was the foundation of stereochemistry by LeBel [6]

Number of known Organic Compounds

(a) (b) (c)

Homogeneity constant melting point

Elemental Composition empirical formula

Test for Functional Groups

Figure 4 CRC Handbook of Chemistry and Physics.

Figure 5 Beilsteins Handbuch der Organischen Chemie.

Information Box 3 Beilsteins Handbuch der Organischen Chemie, 2. Supplementary work,

if it is not a known compound

Such degradation studies required large amounts of the material to be studied in

It is obvious that these experimental aspects restricted structure elucidation to

Stepwise degradation until known compounds are reached

generates an incomplete set of pieces of a structure puzzle

? how to put them together ?

need information on the backbone by (reductive) defunctionalization.

distillation from Zn-dust at 400°C

There was also an important corollary regarding synthesis: confirmation of a

Compounds with only Oxygen Functionalities

Figure 1.1 Albert Szent‐Györgyi

Classical Methods in Structure Elucidation of Natural Products. First Edition, R. W. Hoffmann.

Figure 1.2 (a) Fruits containing

Pentoses and hexoses, therefore carbohydrates in general are dehydrated

1.1 Preliminary Findings. Upon treatment with chloro(triphenyl)methane,

Ascorbic acid readily formed an acetonide [7]. It should, therefore, be a 1,2‐ or

Information Box 2 Zerewitinoff Test for Active Hydrogen [9].

Methyl-Grignard reagents such as CH3MgI react with all compounds