Anodic Oxidation of (Trimethylsilyl)methanes with ?-Electron Substituents in the Presence of Nucleophiles

Article abstract of DOI:10.1246/bcsj.62.219

It was found that oxidation potentials of methanes with ?-electron substituents were decreased by introduction of a trimethylsilyl group.The anodic oxidation of benzyl-, allyl-, aryl(or alkyl)thiomethyl-, and aryloxymethyl-substituted trimethylsilanes smoothly proceeded in the presence of nucleophiles, e.g. alcohols and carboxylic acids, to eliminate the trimethylsilyl groups giving the corresponding alkoxylated and carboxylated products in moderate or high yields without full optimization of electrolytic conditions, while aminomethylsilanes did not undergo such a kind of anodic oxidation.