Electrophilic and Nucleophilic Addition Reactions of α,β-Unsaturated Diphenylphosphoryl Compounds

Abstract

Procedures were developed for the synthesis of diphenyl(prop-1-en-1-yl)phosphine oxide and cyclohex-1-en-1-yl(diphenyl)phosphine oxide by alkaline hydrolysis of triphenyl(prop-1-en-1-yl)phosphonium bromide and cyclohex-1-en-1-yl(triphenyl)phosphonim bromide, respectively. The bromination of diphenyl(vinyl)phosphine oxide, diphenyl(prop-1-en-1-yl)phosphine oxide, and cyclohex-1-en-1-yl(diphenyl)phosphine oxide with excess bromine gave the corresponding 1,2-dibromo derivatives. Dehydrobromination of 1,2-dibromoethyl(diphenyl)phosphine oxide and 1,2-dibromopropyl(diphenyl)phosphine oxide with sodium hydroxide afforded 1-bromoethenyl(diphenyl)phosphine oxide and 1-bromoprop-1-en-1-yl(diphenyl)phosphine oxide. Addition of bromine and methanol to 1-bromoethenyl(diphenyl)phosphine oxide and 1-bromoprop-1-en-1-yl-(diphenyl)phosphine oxide was studied.