Synthesis of thiazolidine-2,5-dithiones: characterisation of 4-substituted thiazolidinedithiones

Abstract

A general method for the synthesis of a series of 4,4-disubstituted thiazolidine-2,5-dithiones (1)–(6) initially consisted in reactions of α-metallated aralkyl isothiocyanates with carbon disulphide. 4-Monosubstituted thiazolidine-2,5-dithiones (7)–(9) are very susceptible to oxidation, changing rapidly into their oxidative dimers. The reason for the unexpected methylation of thiazolidine dithiones (7)–(9) became evident from the results of MNDO calculations.