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Report | Regular issue | Vol 23, No. 5, 1985, pp.1181-1195
Published online, 1st January, 1970
DOI: 10.3987/R-1985-05-1181
Stereospecific Synthesis of Thiazolidine-2-thiones

Ernesto Brunet, M. Carmen Carreño, and José Luis Garcia Ruano*

*Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain


The synthesis of thiazolidine-2-thiones from vic-iodoalkanecarbamates, stereospecifically obtained from cis and trans-butene, is reported. Reaction of the iodo-derivatives with potassium ethylxanthate and sodium hydroxide, allowed the stereospecific formation of thiazolidine-2-thiones. The stereochemistry of the latter reaction could be controlled by the experimental conditions. 4-Phenylthiazolidine-1-thione was obtained from the vic-iodoalkanecarbamate generated from styrene. A separable mixture of thiazolidin-2-ones (major camponent) and thiazolidine-2-thiones was obtained by reduction with NaBH4 from the substitution product of vic-iodoalkanecarbamates with potasium ethylxanthate.