The reactions with amines of disulphides derived from thiazolium salts. Part II. Tertiary and aromatic amines and the thiolation reaction

Abstract

The reaction of thiamine disulphide with triethylamine or with aniline involves nucleophilic cleavage of the disulphide bond as the primary process. Subsequent steps differ from those in the reactions of primary aliphatic amines in that the first-formed enethiol, rather than an enamine, undergoes cyclisation and thiolation to give a thiazolinethione. The source of the sulphur involved in thiolation and the possible nature of the substrate have been investigated.

The fission of disulphides by alcohols is discussed, and also their anomalous reaction with NN-dimethylaniline leading to a thiazolinone and thiochrome.