Some phenyl migrations in organophosphorus compounds

Abstract

Alkaline hydrolyses of buta-1,3-dien-1-yltriphenylphosphonium bromide, triphenyl-2-phenylvinylphosphonium bromide, methyldiphenyl-2-phenylvinylphosphonium bromide, and halomethyltriphenylphosphonium halides are accompanied by phenyl migration from phosphorus to adjacent carbon. It is suggested that this migration is explained by the presence on the α-carbon atom of an electron-delocalizing substituent or a good leaving group.

Under carefully controlled conditions phenylphosphonous dichloride reacts with benzophenone to give phenyltriphenylmethylphosphinic chloride. The reaction of triphenylmethanol with phenylphosphonous dichloride gives low yields of benzophenone together with the same acid chloride.