Reactions of sulphenyl chlorides and disulphides in acidic media. Trapping of alkyl(bisalkylthio)sulphonium ion intermediates

Abstract

A ¹H n.m.r. study of the reaction between alkanesulphenyl chlorides and dialkyl disulphides in sulphur dioxide in the presence of Lewis acids and in strong acids (FSO₃H or 98% of H₂SO₄) led to the characterization of alkyl-(bisalkylthio)sulphonium ions R[graphic omitted](SR)₂(1). Results of conductimetric and ¹H n.m.r. experiments at low temperatures suggest that the formation of (1) also occurs to a large extent in the absence of Lewis acids. It was observed that ions (1) are also formed from disulphides by the action of strong acids.