REACTIONS WITH AMINES OF DISULPHIDES DERIVED FROM THIAZOLIUM SALTS .I. PRIMARY AND SECONDARY AMINES

The reaction with primary amines of disulphides derived from base-catalysed ring-opening of thiazolium salts proceeds by nucleophilic cleavage of the disulphide bond and enamine formation, and finally yields an imidazolinethione as major product. Evidence for this mode of amine attack and for the presence of enamine and enethiol intermediates was found in the reaction of various modified disulphides, the reaction with secondary amines, and the reaction of a postulated intermediate. The relationship between this reaction and those involved in the conversion of thiazolium salts into imidazolium salts in aqueous solution is considered.