Organophosphorus compounds. IX. Vinylphosphonium salts as reagents for proteins

Abstract

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 NHCH₂CH_2-÷PAr₃ and SCH₂CH₂- ⁺PAr₃ respectively.