Anodic oxidation of organophosphorus compounds. Part 1. Anodic alkylamination of triphenylphosphine

Abstract

Anodic oxidation of triphenylphosphine has been investigated by cyclic voltammetry and controlled potential electrolysis at a glassy-carbon electrode in acetonitrile. Electrolyses of triphenylphosphine in the presence of various primary amines result in the formation of monoalkylaminotriphenylphosphonium salts in 50–70% yield. The reaction sequence is suggested to be one-electron oxidation of the phosphine, nucleophilic attack of primary amine on the resulting cation radical, and a further one-electron transfer and loss of a proton.