J . Org. Chem.

1986,51, 567-569 567

Registry No. 1 (x = I), 10364-05-3;1 (x = Br), 89566-55-2; Our HOCl scavenger was 35% HzOz, which reduces
1 (X = CN), 80745-57-9; 1 (X = Cl), 89566-54-1;1 (X = OCOCHJ, HOCl according to eq 3; without formation of organic side
74467-16-6; 1 (X = F), 78385-89-4;1 (X = CF3), 94994-04-4;1 (X products.
= C=CSi(CH,)3), 94994-11-3;1 (x = COCH3),99631-72-8;I (x
= COOCH3),94994-00-0;1 (x = OCH,), 74467-18-8;1 (x = Sn- HOCl + H202 -+ HC1+ 02 + HzO (3)
(CH3)3),84010-82-2;1 (X = P-FCsH4),61541-35-3;I (X = CsH,),
55044-15-0; 1 (X = H), 931-98-6;1 (X = NHCOCH3),80745-58-0; Best reaction conditions were achieved by working in
1 (X = p-CH30CtjH$, 99631-73-9;1 (X = CON(CH3)2),80745-59-1; a weakly acidic medium, where oxidation was rapid with
1 (x = Si(CH3),),99631-74-0; 1 (x = CH,), 55044-63-8; 1 (x = no competitive reduction of HC102 to HOCl (eq 4).5
N(CH&), 80745-60-4; 1 (x = C(CH,),), 94994-05-5; 4 (x = Si- HC10z + HzO2 4 HOCl + H2O + 02 (4)
(CH3)3),95552-61-7;4 (x = SXI(CH~)~), 78385-88-3.
2C102 + H202 -+ 2HC102 + 02 (5)
Under these conditions, any chlorine dioxide is reduced
Selective Oxidation of Aldehydes to Carboxylic to chlorous acid (eq 5).6J0
Acids with Sodium Chlorite-Hydrogen Peroxide Reactions were carried out by addition of 1.1-1.4 mol
Enrico Dalcanale* equiv of aqueous NaC102to a solution of aldehyde and 1.04
mol equiv of 35% H202in aqueous acetonitrile, at 20 “C,
Zstituto “Guido Donegani”, 28100 Nouara, Italy buffered with NaH,P04 at pH 4.3. The addition of Na-
Fernando Montanari* CIOz required 1-2 h, and the reaction was complete after
Centro C N R and Dipartimento di Chimica Organica e
another 1-5 h depending on the aldehyde (procedure A).
Zndustriale dell’Universitti, 20133 Milano, Italy With the most sensitive substrates more H202(up to 5 mol
equiv) and a lower pH (-2) were required, in order to
Received J u l y 23, 1985 speed up HOCl reduction by HzOz. In a few instances
Several methods for the oxidation of aldehydes to the carboxylic acids quantitatively precipitated and were di-
corresponding carboxylic acids are known.lV2 However, rectly filtered from the reaction medium. In most cases
no one seems to be completely satisfactory, the major isolated yields were very high for satisfactorily pure
drawbacks being high costs, low selectivities, and complex products (Table I).
operating conditions. Their application to large-scale Following this procedure P-aryl-substituted a$-unsat-
preparations is therefore difficult. urated aldehydes are oxidized to the corresponding car-
We thus addressed our attention to the use of the boxylic acids without affecting the olefinic double bond
inexpensive sodium chlorite? which reacts with aldehydes (entries 1-5). Yields are lower with aliphatic a,@-unsatu-
under very mild conditions to give carboxylic acids (eq 1). rated and/or more hydrophilic aldehydes (entries 19, 20).
In the presence of an electron donor group in P-position
+
RCHO HClO2 RCOOH HOCl 4 + (1) (entry 21), chlorination of the double bond becomes pre-
However, hypochlorite ion must be removed in order to dominant. The same occurs in the presence of isolated
avoid side reactions, since the redox pair HOCl/Cl- is a double bonds (entry 22). Triple bonds directly linked to
more powerful oxidant than C102-/HOC1.4 Another the aldehyde group are substantially stable under these
drawback is the oxidation of C10, to C102according to conditions. For example, phenylpropargylic aldehyde is
eq 2.3a35 converted into the corresponding carboxylic acid, together
+
HOCl 2C102- 2C102 + C1- + OH-
4 (2) with only small amounts of benzoic acid (entry 6).
The method reported here is of general application to
2-Methy1-2-butene,’@ and sulfamic acidw9 aromatic aldehydes, including those which are incompat-
have been tested as HOCl scavengers. 2-Methyl-2-butene ible2bwith HOCl (entries 7-9). Heterocyclic aldehydes are
must be used in a very large excess. Resorcinol is con- good substrates (entries 14-16), except for those which are
verted into 4-chloro-l,3-dihydroxybenzene, which must be sensitive to the acidic medium like pyrroles (entry 18).
removed from the reaction mixture. Sulfamic acid works Furfural gives mainly 2-furoic acid with small quantities
well in the oxidation of hydroxylated aromatic aldehydes, of maleic acid as a side product (entry 17).11 p-Amino-
but it gave poor results in the case of a,O-unsaturated benzaldehyde affords only tars (entry 12). In p-methyl-
aldehydes (see below). thiobenzaldehyde, oxidation of the aldehyde group is ac-
companied by the concomitant oxidation of sulfide to a
(1) (a) Augustine, R. L. “Oxidation”; Dekker, Inc.: New York, 1969; mixture of sulfoxide and sulfone (entry 13).
Vol. I, pp 81-86. (b) Buehler, C. A.; Pearson, D. E. “Survey of Organic
Synthesis”; Wiley: New York, 1970; Vol. I, pp 76C-764; 1977, Vol. 11, p The effect of various organic solvents was checked with
669. (c) March, J. “Advanced Organic Chemistry”, 2nd ed.; McGraw Hill: cinnamaldehyde as substrate. Results are summarized in
New York, 1977; p 641-643. (d) Houben-Weyl “Methoden der Organis- Table 11.
chen Chemie”,Bd E 3, “Aldehyde”; Farbe, J. Ed; Georg Thieme Verlag: The yield was increased using less hydrophilic alcohols
Stuttgart, 1983; pp 634-635. (e) Dehmlow, E. V.; Dehmlow, S. S.
“Phase-Transfer Catalysis”, 2nd ed.; Verlag Chemie: Weinheim, 1983; (entries 1-4). Toluene (entry 5) greatly reduced the re-
pp 295-321. action rate, requiring 24 h for complete conversion of the
(2) (a) Ganem, B.; Heggs, R. P., Biloski, A. J.; Schwartz, D. R. Tet- substrate.
rahedron Lett. 1980,21,685-688. (b) Nwaukwa, S. 0.; Keehn, P. M. Ibid.
1982,23,3131-3134. (c) Scholz, D. Monatsh. Chem. 1979,110,1471-1473. For aldehydes in which reaction of HOCl with the sub-
(3) (a) Lindgren, B. 0.; Nilsson, T. Acta Chem. Scand. 1973, 27, strate is faster than reaction with H202(Table I, entries
888-890. (b) Kudesia, V. P. Bull. SOC.Chim. Belg. 1972,81, 623-628. 10, l l ) , dimethyl sulfoxide (Me2SO) proved to be an ef-
( 4 ) Holst, G. Chem. Rev. 1954,54, 169-194.
( 5 ) Reaction 4 is very slow in the pH range 3.5-9.0 and at low tem- fective HOCl scavenger when used as solvent, since it is
peratures.6
(6) Kirk-Othmer “Encyclopedia of Chemical Technology”, 3rd ed.;
Wiley: New York, 1979; Vol. V, pp 585-632. (10) MacMahon, J. D. US.Patent 2358866,1944; Chem. Abstr. 1945,
(7) (a) Bal, B. S.; Childers, W. E.; Pinnik, H. W. Tetrahedron 1981, 39, 1740.
37,2091-2096. (b) Kraus, G. A.; Tashner, M. J. J. Org. Chem. 1980,45, (11)Furfural doesn’t react with HzOzalone under these conditions.
1175-1176. (c) Kraus, G. A.; Roth, B. Ibid. 4825-4830. However 2,5-di-tert-butylfuran is oxidized by NaOCl to 2,2,7,7-tetra-
(8) Arora, G. S.; Shirahama, H.; Mataumato, T. Chem. Ind. 1983,318. methyl-4-0ctene-3,6-dione.~~
(9) Colombo, L.; Gennari, C.; Santandrea, M.; Narisano, E.; Scolastico, (12) Fitzpatrich, J. E.; Milner, D. J.; White, P. Synth. Common.1982,
C. J. Chem. Soc., Perkin Trans. 1 1980, 136-140. 12, 489-494.

0022-3263/86/1951-0567$01.50/0 0 1986 American Chemical Society

56% J . Org. Chem., Vol. 51, No. 4 , 1986 Notes

Table I. Oxidation of Aldehydes to Carboxylic Acids with NaC102-HzOzn

carboxylic acid
entry substrateb procedure isolated yields, % mp, "C'
1 CsH,CH=CHCHO A 95d 131-133 (133)
2 CGH&H=C(CH3)CHO A 93' 76-80 (79-81)
3 CGH&H=C( C1)CHO A 93f 135-136 (137-138)
4 C&,CH=C(Br)CHO A 949 129-130 (131-132)
5 o-O~NCGH,CH=CHCHO A 98 240-241 (240)
6 CcHsCZCCHO B 74h 135-136 (137)
r
C,H,CHO .4' 93 120-121 (122)
8 p-CH,OC,jH,CHO 4 86 183-184 (184)
9 p-CH3CONHCsH4CHO A' 98 258-259 (259-262)
10 p-HOC,H,CHO B "fn
212-213 (213-214)
11 2-OH-3-(OCH,)C6H,CHO A, B n
12 p-H2NC,H,CHO A, €3 0
13 p-CH3SCsH,CHO AP 1009
14 pyridine-4-carboxaldehyde A 100' 313-315 (315)
15 thiophene- 2-carboxaldehyde A 94 127-129 (129-130)
16 5-nitrofuran-2-carboxaldehyde B 84 183 (184)
17 furan-2-carboxaldehyde B 82s 131-133 (133-134)
18 pyrrole-2-carboxaldehyde A,B 0
19 CH3CHZCHzCH=CHCHO A 88 36-37 (36-37)
20 CH,CH=CHCHO B 53' 71-72 (72)
21 C2HSOCH=C(CH,)CHO A,B n
22 (CH3)2C=CH(CH2)2C(CH3)=CHCH0 (cis and trans) AB n
23 CHJ!HZCHZCH2CH2CHO A 96 127-129 (760 torr)
24 ~-CH~CGH,CHO A 91 101-103 (102-103)
a Acetonitrile as solvent, unless otherwise stated. a$-Unsaturated aldehydes and acids are E diastereoisomers, unless otherwise stated.
Crude products. In parenthesis, mp or bp values from the 1iterat~re.l~ d A small amount (<2%) of P-chlorostyrene was also formed. Mass
spectrum, m / e 138 (M+), 103 (loo%), 77, 51. "H NMR (CDCl,) 6 2.11 (d, 3 H), 7.32 (d, 5 H), 7.75 (d, 1 H), 11.70 (s, 1 H). f l H NMR
(CDC1,) 6 7.30-7.61 (m; 3 H), 7.70-7.96 (m, 2 H), 8.00 (s, 1 H), 12.50 (s, 1 H). glH NMR (CDC1,) 6 7.25-7.55 (m, 3 H), 7.65-8.05 (m, 2 H),
8.31 (s, 1 H), 12.30 (s, 1 H). hBenzoic acid (6%) was also formed. 'CHSOH as solvent. 'CH,OH-CH,CN 1:l as solvents. "'Hydroquinone
(27%), mp 170 "C, was the main product, together with chlorinated compounds and tars. "Chlorinated compounds, only. OTars. PMolar
ratio NaCIOz-aldehyde 1:l. Gas chromatographic yields: mixture of p-CH3SOCGH4COOH(75% ), and p-CH3S02C6H4COOH(25%) ('H
NMR analysis). Mass spectra (methyl esters): sulfoxide, m / e 198 (M'), 183, 151 (loo%), 77, 59, 45; sulfone, m / e 214 (M+), 198, 183, 151
(loo%), 77, 59, 45. 'Mass spectrum (methyl ester): m / e 137 (M+), 106, 78 (loo%), 59. "aleic acid (15%), mp 129-130 "C, was also
formed. ' No other products except tars were detected.

Table 11. Oxidation of Cinnamaldehyde with NaC1Oz-H2Oz Table 111. Oxidation of Aldehydes to Carboxylic Acids
in Various Solvents with NaCIOI-MelSO
entry solvent isolated yields, 70 carboxylic acid
1 MeOH 89 isolated
2 EtOH 91 entry substrate yields, 70 mp; "C
3 i-BuOH 95 1 CCHSCH=CHCHO 95 130-132 (133)
4 t-BuOH 95 2 p-HOCGH,CHO 86 211-214 (213-214)
5 Toluene 95 3 2-HO-3-(CH3O)C,H,CHO 83 148-149 (152)
6 9;i 4 (CH,)zC=CH(CH2)2C(C- 46'
H,)=CHCHO (cis and
oxidized to dimethyl sulfone. Results are summarized in trans)
Table 111. 5 cyclohex-3-ene 30d
Me2S0works well with a$-unsaturated aldehydes, such carboxaldehyde
as cinnamaldehyde (entry l),and with aromatic hydroxy 'Crude products. In parentheses, melting point values from the
aldehydes (entries 2,3). Fair results were obtained in the l i t e r a t ~ r e . ' ~E / Z = 58:42. Gas chromatographic yields at 67%
presence of isolated C=C double bonds (entries 4,5). In conversion: E / Z = 71:29. With an aldehyde/NaCIOz 1:3 molar
all cases, reaction rates were lower and the workup more ratio, only a 30% yield of carboxylic acids ( E / Z = 70:30) was ob-
difficult than for reactions carried out in the presence of served at 100% conversion, the remaining being chlorinated com-
H20z. It must be noted that, in the oxidation of cinnam- pounds. Gas chromatographic yields, the remaining being chlo-
rinated and hydroxylated compounds.
aldehyde, sulfamic acid was also tested as HOC1 scavenger:
cinnamic acid was isolated in fair yields (60%), together MAT-GC/MS spectrometer and IR spectra with Pye-
with minor amounts of cinnamonitrile. Unicam SP3-100 spectrophotometer. GLC analyses were
In conclusion, the use of the inexpensive pair NaC1- performed on Hewlett-Packard Models 7620 A and 5830
OZ-H2O2or, in some cases, of NaC102-Me2S0, allows mild A flame-ionization instruments with Supelco SP-2100
oxidation of a wide range of aromatic, aliphatic, and columns. Melting points were measured on a Buchi-Tottoli
heterocyclic aldehydes to the corresponding carboxylic apparatus and are uncorrected.
acids. This method is particularly useful for substrates Organic and inorganic reagents, ACS grade, were used
in which other oxidation methods fail or require complex without further purification. All products were identified
and expensive reaction conditions. through their mp, lH NMR spectra, and/or IR and MS
spectra.
Experimental Section General Oxidation Procedures. Procedure A. A
IH NMR Spectra were recorded a t 60 and 90 MHz on solution of 8.0 g (7.0 X mol) of NaC102 (79% purity,
Hitachi Perkin-Elmer R-24 B and Brucker W-90 spec- by iodometric titration) in 70 mL of water was added
trometers, respectively, with Me,Si as internal standard. dropwise in 2 h to a stirred mixture of 6.6 g (5 X mol)
Mass spectra were obtained with a CHS-DF Varian of cinnamaldehyde (99% purity) in 50 mL of acetonitrile
 J. Org. Chem. 1986,51, 569-571 569

and 1.6 g of NaH2P04in 20 mL of water and 5.0 mL (5.2 dine-4-carboxaldehyde, 812-85-5; thiophene-2-carboxaldehyde,
x mol) of 35% HzOz,keeping the temperature at 10 98-03-3; 5-nitro-2-furancarboxaldehyde,698-63-5; furan-2-
"C with water cooling. Oxygen evolved from the solution carboxaldehyde, 98-01-1; pyrole-2-carboxaldehyde,1003-29-8;
hydroquinone, 123-31-9;methyl ppidine-4-carboxylate,2459-09-8;
was monitored until the end of the reaction (about 1 h) 5-nitro-2-furancarboxylic acid, 645-12-5; 2-furancarboxylic acid,
with a bubbler connected to the apparatus. A small 88-14-2; maleic acid, 110-16-7; cyclohexene-3-carboxaldehyde,
amount (-0.5 g) of NaZSO3was added to destroy the 100-50-5;cyclohexene-3-carboxylicacid, 4771-80-6; thiophene-2-
unreacted HOC1 and HzOz. Acidification with 10% carboxylic acid, 527-72-0.
aqueous HC1 afforded 7.0 g (95%) of cinnamic acid, as
crystalline solid, mp 131-133 "C (lit.13mp 133 "C). TLC
and GLC analyses revealed not valuable impurities. 'H
NMR (CDCl,) 6 6.41 (d, 1 H), 7.17-7.69 (m, 5 H), 7.73 (d,
1 H), 11.85 (s, 1 H).
Procedure B. It differs from procedure A since a 5:l Synthesis of Novel GH-1,3-OxazineDerivatives
molar ratio H,O,-aldehyde is used, and the pH of the with Perfluoroalkyl Substituents
medium is lowered to about 2.0 by cautious addition of
37% HC1 to the NaHzP04buffer. The reactions are faster Isao Ikeda,* Mitsuhiro Umino, and Mitsuo Okahara
than those of procedure A.
General Oxidation Procedure with NaC1O2-Me2SO. Department of Applied Chemistry, Faculty of Engineering,
A solution of 8.0 g (7.0 X mol) of 79% NaCIOz (io- Osaka University, Yamadaoka 2-1, Suita, Osaka, J a p a n 565
dometric titration) in 70 mL of HzO was added dropwise
in 2 h a t room temperature to a stirred mixture of 6.6 g Received October 2, 1985
(5.0 X mol) of cinnamaldehyde in 50 mL of MezSO
and of 1.6 g of NaH2P04in 20 mL of water. The mixture Recently, the reactions of perfluoro-2-methylpent-2-ene
was left overnight at room temperature, then 5% aqueous ( 1),1,2a dimer of hexafluoropropene, with various nucleo-
solution of NaHCO, was added. The aqueous phase was philes such as alcohols, carboxylic acids, amines and thiols
extracted 3 times with CHZCl2and acidified with 10 M (or their conjugate bases) have been inve~tigated,,,~ and
aqueous HC1, and the precipitated cinnamic acid was it has been reported that the reaction proceeded via an
collected: 7.0 g (95% yield), mp 130-132 "C. TLC and apparent nucleophilic substitution reaction.
GLC analyses revealed no appreciable impurity nor con- The reaction of 1 as a 1,3-bidentate electrophile has been
tamination from Me,SO or dimethyl sulphone. studied in recent years and various heterocycles with five-,
General Oxidation Procedure with NaC10,- six-, seven-, and eight-membered rings resulted from the
H2NS03H. The general procedure A was followed, but reactions with bidentate nucleophiles such as N,N-di-
6.3 g (6.5 X mol) of sulfamic acid as scavenger dis- methylhydra~ine,~ acylhydrazones,6 benzoylacetonitrile,
solved in 60 mL of water and 6.6 g (5 X lo-' mol) of cin- benzoyltrifluoroacetone, acetoacetanilide, catechol, o-
namaldehyde in 50 mL of tert-butyl alcohol was used. phenylenediamine, o-aminophenol, and sali~ylaldehyde.~-~
After 2 h at room temperature, a crude product was iso- In the present work, new 6H-1,3-oxazines with per-
lated and purified by column chromatography (silica gel; fluoroalkyl substituents (3a-d) were obtained in moderate
8:2 ethyl ether-n-hexane): 4.4 g ( 6 0 % ) of cinnamic acid, yields from 2 and 1 in the presence of base.
mp 131-133 "C, 1.64 g (25%) of cinnamonitrile, mp 20 "C
(lit.', mp 20-21 "C), and 0.1 g (1.2%) of tert-butyl cin- Results and Discussion
namate, bp 70 "C (0.1 torr) (lit.', bp 140 "C (9 torr)).
When a tetrahydrofuran (THF) solution of 1 was treated
Acknowledgment. We are grateful to Dr. R. Santi for with a THF suspension of the sodium salt of 2a, a single
helpful discussions and to Mrs. T. Fiorani for determina- oxazine was cleanly formed as demonstrated by "F NMR.
tion of the mass spectra. The spectrum of the product showed the presence of only
Registry No. (E)-C6H5CH=CHCH0, 14371-10-9; ( E ) - one pentafluoroethyl, one trifluoromethyl, and one di-
C6H,CH=C(CH,)CHO, 15174-47-7; (E)-C,HbCH=C(Cl)CHO, fluoromethylene group. However, spectral data did not
99414-74-1; (E)-C6H5CH=C(Br)CH0, 99686-39-2; (E)-o- rule out one of the two possible structures (3a and 4a). To
02NC6H,CH=CHCHO, 66894-06-2; P - C H ~ C O N H C ~ H ~ C H O ,
122-85-0; p-HOC6H4CHO, 123-08-0; (E)-CH&H=CHCHO,
distinguish between these two possibilities, the product was
123-73-9; (E)-CZHSOCH=C(CH3)CHO, 62055-46-3; (2)- treated with l,l-dimethylhydrazine.'O The I9F NMR
(CH,),C=CH(CH2)2C(CH3)=CHCHO,106-26-3;(E)-(CH,)zC= spectrum of the resulting compound showed the disap-
CH(CH2)2C(CHJ=CHCHO, 141-27-5; CH3(CH2)4CHO,66-25-1; pearance of two fluorine atoms from the original product
(E)-C6H&H=CHCO2H, 140-10-3; (E)-C6H,CH=C(CH,)CO2H, (3a or 4a);a band assigned to carbonyl absorption (1720
1895-97-2; (E)-C6H&H=C(Cl)CO,H, 705-55-5; (E)-CBH~CH= cm-l) appeared in the IR spectrum. Furthermore, the mass
C(Br)CO2H, 15894-30-1; ( E ) - O - ~ ~ N C ~ H , C H = C H C O882-06-4;
~H, spectrum of the dimethylhydrazine-treated product dis-
C~HSCZCCO~H 637-44-5;
, P - C H ~ C O N H C ~ H ~ C O556-08-1;
~H, played a very strong fragment of relative abundance of 69
P - C H ~ S O C ~ H ~ C O33963-58-5;
~H, P - C H ~ S O ~ C ~ H ~ C4052-30-6;
O~H,
( E )- C H3 ( C Hz)2CH=C HC 02H , 134 19-69-7 ; ( E )- C H3C H =
CHCOZH, 107-93-7; 2-HO-3-CH3OC6H,COzH, 877-22-5; ( E ) -
(1) Du Pont US. Patent 2918501, 1959.
(CH3)2C=CH( CH2)SC (CH,)=CHC02H, 4698-08-2; (2)- (2) Dresdner, R. D.; Tlumac, F. N.; Young, J. A. J . Org. Chem. 1965,
(CH3)2C=CH(CHz)zC(CH3)=CHC02H, 4613-38-1; C6H5C<<- 30,3524.
tbdCCHO, 2579-22-8; C6H5CH0, 100-52-7; p-CH30C6H4CH0, (3) Ishikawa, N.; Nagashima, A. Bull. Chem. SOC.Jpn. 1976,49, 502.
123-11-5; 2-OH-3-(OCHJC6H&HO, 148-53-8; P - H z N C ~ H ~ C H O , (4) Yanagida, S.; Noji, Y.; Okahara, M. Tetrahedron Lett. 1977, 2337.
556-18-3; P - C H ~ S C ~ H ~ C H
3446-89-7;
O, 2-CH&H4CHO, 529-20-4; (5) Ikeda, I.; Tsukamoto, T.; Okahara, M. Chem. Lett. 1980, 583.
C6H,COpH, 65-85-0; P - C H ~ C O C ~ H , C O ~100-09-4;
H, CH3(CH2)4- (6) Ikeda, I.; Kogame, Y.; Okahara, M. J . Org. Chem. 1985, 50, 3640.
(7) Flowers, W. T.; Haszeldine, R. N.; Owen, C. R.; Thomas, A. J.
COzH, 142-62-1; 2-CH3C6H4C02H,118-90-1; NaC1OZ,7758-19-2; Chem. SOC.,Chem. Commun. 1974, 134.
HzOz, 7722-84-1; Me2S0, 67-68-5; H2NS03H, 5329-14-6; pyri- (8) Maruta, M.; Kubota, S.; Yoshimura, N.; Kitazume, T.; Ishikawa,
N. J. Fluorine Chem. 1980, 16, 75.
(9) Maruta, M.; Kubota, S.; Yoshimura, N.; Kitazume, T.; Ishikawa,
(13) Buckingham, J. "Dictionary of Organic Compounds=, 5th ed.; N. Chem. Lett. 1979, 291.
Chapman and Hall: New York, 1982. (10) Zentmyer, D. T.; Wagner, E. C. J . Org. Chem. 1949, 14, 967.

0022-3263/86/ 1951-0569$01.50/0 0 1986 American Chemical Society