Some reactions of diphenyl-1-phenylvinylphosphine

Abstract

Diphenyl-1-phenylvinylphosphine has been obtained from sodium diphenylphosphide and α-bromostyrene. The betaine formed from the phosphine and acrylonitrile cyclises to a five-membered ylid but with styrene oxide the initial betaine does not cyclise and in ethanol gives largely styrene and diphenylstyrylphosphine oxide. Methyldiphenyl-1-phenylvinylphosphonium iodide adds diphenylphosphide anion to give the ylid MePh₂[graphic omitted]·Ph·CH₂·PPh₂, and with butyl-lithium gives a methylene ylid which cyclises to a four-membered ylid. In all cases the ylids were detected by their reactions with aldehydes.