Reaction of Olefins with Anodically Generated Radical Cations of Trialkyl Phosphites and Dialkyl Trimethylsilyl Phosphites

Abstract

Electrochemical oxidation of trialkyl phosphites and dialkyl trimethylsilyl phosphites in the presence of olefins yields mixtures of isomeric dialkyl alkenyl(cycloalkenyl)phosphonates with predominating [alken(cycloalken)-2-yl]phosphonates. A scheme of the process was proposed, which involves attack of the alkene double bond by anodically generated radical cations of phosphites, followed by a second electron transfer, deprotonation, and elimination of cationic species: alkyl cation in the case of trialkyl phosphites and trimethylsilyl cation in the case trimethylsilyl phosphites.