4‐thiazohne‐2‐thiones. III. The thermodynamic stability of intermediate, tautomeric thiazolidines and dithiocarbamates

Abstract

Abstract The intermediate products isolated from preparations of 3‐substituted 4‐thiazoline‐2‐thiones by the reaction of primary amines, carbon disulfide, and α‐haloketones may be either 4‐hydroxy‐thiazolidine‐2‐thiones or dithiocarbamates. Tautomeric equilibrium of the two types of intermediates in solution is demonstrated, and the more thermodynamically stable form is determined. Steric and electronic effects of substitution on stability are described.