Reactions of bromonitroalkenes with tervalent phosphorus. Part I. Reaction in aprotic solvents
Abstract
The reaction of a variety of 2-substituted 1-bromo-1-nitroethylenes with triphenylphosphine in benzene or ethyl acetate gave good yields of cyanomethyl(triphenyl)phosphonium salts, which on treatment with base afforded the corresponding ylides. An analogous cyanomethylphosphonate was obtained from a reaction with triethyl phosphite. Three alternative sites of initial attack by phosphine are considered in an attempt to explain the deoxygenation reaction; efforts to gain evidence for one of these (initial attack at halogen) were only partially successful.