Reactions of carbonyl compounds with tervalent phosphorus reagents. Part VI. Benzoate esters and halogenophosphines

Abstract

Chloro(di-t-butyl)phosphine reacts with alkyl benzoates to give phosphine oxides, alkyl chlorides, and aroyl chlorides. Kinetic and other evidence is presented for a mechanism involving rate-determining, competing nucleophilic attack by the phosphine at the alkyl and carbonyl carbon atoms of the esters. Reactions of methyl diphenyl-phosphinite with benzoyl and acetyl chlorides are discussed, and the products are related to addition reactions of acyldiphenylphosphine oxides.