Anodic Oxidation of Organophosphorus Compounds. III. Anodic Alkoxylation and Thioalkoxylation of Triphenylphosphine

Abstract

Controlled potential electrolysis of triphenylphosphine in acetonitrile containing various primary alcohols and dialkyldisulfides resulted in the formation of the corresponding alkoxy and alkylthio triphenylphosphonium salts, [Ph₃P⁺-X] [ClO₄^-]. Compounds with X=OMe, OEt, OPrⁿ, SMe, SEt, and SPrⁿ were isolated. The alkoxy derivatives reacted with imidazole and thiophenol under mild conditions to give the corresponding N- and S-alkylated products quantitatively.