Thiazolinium salts and their reactions with nucleophiles

Abstract

2,3-Dialkyl- and 3-alkyl-2-aryl-2-thiazolinium salts were prepared by quaternisation of the corresponding 2-thiazolines. Some 3-alkyl-2-alkylthio-2-thiazolinium salts were obtained by quaternisation of 2-alkylthio-2-thiazolines; the products included bicyclic salts obtained from αω-dibromides and 2-thiazoline-2-thiol. In some cases attempted quaternisation yielded only the 3-alkylthiazolidine-2-thiones, the original S-alkyl residue being lost. The behaviour of the salts with nucleophiles such as water, base, borohydride ion, and benzenethiolate ion was investigated. The oxidation of 2-thiazoline-2-thiol was also studied.