The Synthesis of 1,3-Dithiolane-2-thione Derivatives

Article abstract of DOI:10.1246/bcsj.60.727

The reaction of 2,2-dimethylthiirane with carbon disulfide in the presence of triethylamine was accelerated under high pressure to give 4,4-dimethyl-1,3-dithiolane-2-thione nearly quantitatively.The activation volume of this reaction at 40 deg C was estimated to be -41 ml mol^-1.The rate of the reaction was proportional to the amount of triethylamine when a limited amount of triethylamine was used.The reaction of 2-methylthiirane, 2-hexylthiirane, 1,2-epithiocyclohexane, and 2-phenylthiirane with carbon disulfide gave the corresponding 1,3-dithiolane-2-thione derivatives in good yields. 2-Chloromethylthiirane was less reactive to carbon disulfide than other thiiranes under high pressure.Tertiary amines such as N,N-dimethylethylamine, pyridine, and N-methylmorpholine were good catalysts of the reaction.