Affordable Access

Publisher Website

Anodic oxidation of α,α′-bis(trimethylsilyl)xylenes in alcohols

Authors
Journal
Electrochimica Acta
0013-4686
Publisher
Elsevier
Publication Date
Volume
33
Issue
11
Identifiers
DOI: 10.1016/0013-4686(88)80236-6

Abstract

Abstract Anodic oxidation of α,α′-bis(trimethylsilyl)−0-, - m-, and ( p-xylenes ( 1–3) was comparatively examined, α-Trimethylsilylation of xylenes markedly decreased their oxidation potentials while additional α-trimethylsilylation resulted in no further change. The silylxylenes 1–3 underwent anodic alkoxylation in various alcohols accompanying elimination of a trimethylsilyl group to provide the corresponding monoalkoxylated products solely. The efficiency of alkoxylation greatly depended not only on the molecular structures of the substrates but also on those of alcohols and counter anions of supporting electrolytes. From the results, it was suggested that the anodic substitution with alcohols was greatly affected not only by the nature of stabilization of cationic intermediates but also by steric hinderance and electrostatic interaction between the trimethylsilyl group and alcohols as nucleophiles.

There are no comments yet on this publication. Be the first to share your thoughts.