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Reactivity at Different Sites On Metal-Arene Complexes A Classic Example of Umpolung

This document discusses several examples of reactivity in organometallic complexes: 1. Reactivity at different sites on metal-arene complexes can be controlled through electronic effects in a process known as umpolung. 2. Stereospecific introduction of a methyl group can occur in compounds of the morphine type using chromium complexes. 3. Reductive elimination and oxidative addition reactions involving palladium complexes can introduce or remove aryl groups from substrates in a stereocontrolled manner.

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Lurthu Pushparaj
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60 views1 page

Reactivity at Different Sites On Metal-Arene Complexes A Classic Example of Umpolung

This document discusses several examples of reactivity in organometallic complexes: 1. Reactivity at different sites on metal-arene complexes can be controlled through electronic effects in a process known as umpolung. 2. Stereospecific introduction of a methyl group can occur in compounds of the morphine type using chromium complexes. 3. Reductive elimination and oxidative addition reactions involving palladium complexes can introduce or remove aryl groups from substrates in a stereocontrolled manner.

Uploaded by

Lurthu Pushparaj
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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enhanced

nucleophilic increased
substitution tendency for
solvolysis
X

H
enhanced R
acidity H
M
enhanced
acidity
increase in
steric hindrance

Reactivity at different sites on metal-arene complexes; a classic example of umpolung.

RO RO
Cr(CO)3 Cr(CO)3

Me
(i) NaN(TMS)2
O NMe O
(ii) MeI NMe

RO RO

Stereospecific introduction of a methyl group in compounds of the morphine type.

H X
Ar X
LnPd
reductive oxidative
elimination addition
start
of H-X of Ar-X
here

L L

H Pd X Ar Pd X

L L

ArC(O)OR CO
O L
migratory
nucleophilic
C Pd X insertion
abstraction ROH of CO
with ROH Ar
L

Nucleophilic abstraction of σ-acyl-Pd complexes (R = alkyl, X = Cl, Br, I).

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