Reaction of nucleophiles with some 2-alkylthio- and 2-acylthio-3-alkylthiazolium salts

Abstract

2-Alkylthio-3-alkylthiazolium salts were prepared by alkylation of either 2-alkylthiothiazoles or 3-alkyl-Δ⁴-thiazoline-2-thiones; 2-acylthio-3-alkylthiazolium salts were prepared by alkylation of 2-acylthiothiazoles only. The action of a variety of nucleophiles on both species was investigated: attack took place either at C-2 of the thiazole nucleus or at the carbon atom adjacent to sulphur in the 2-substituent, depending on the nature of the nucleophile and of the 2-S-substituent.