Issue 0, 1981

Studies on the structure of some derivatives of 1,3-thiazolidine-2-thione and Δ2-1,3-thiazoline-2-thiol

Abstract

Two types of reactions have been observed for the ambident anion of 1,3-thiazolidine-2-thione: regioselective N-acylation and S-alkylation. The structures of the products, amides and thioethers, were determined by X-ray crystallographic analysis and by assignment of the 13C n.m.r. chemical shifts. The regioselectivity of the reactions is rationalised in terms of the hard–soft acid-base principle and has been exemplified by model experiments.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1981, 914-919

Studies on the structure of some derivatives of 1,3-thiazolidine-2-thione and Δ2-1,3-thiazoline-2-thiol

E. Fujita, Y. Nagao, K. Seno, S. Takao, T. Miyasaka, M. Kimura and W. H. Watson, J. Chem. Soc., Perkin Trans. 1, 1981, 914 DOI: 10.1039/P19810000914

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