Organophosphorus compounds. IX. Vinylphosphonium salts as reagents for proteins

Triarylvinylphosphonium salts are investigated as potential reagents for the radioactive labelling of immunoglobulins and other proteins. A new synthetic route to these vinylphosphonium salts via hydroxyethyl and chloroethyl derivatives is reported. The addition reactions of the vinylphosphonium salts with amines, thiols, and proteins are described and the effects of substituents discussed. In these reactions the functional groups NH2 and SH are replaced by NHCH2CH2-÷PAr3 and SCH2CH2- +PAr3 respectively.