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Note | Regular issue | Vol 45, No. 10, 1997, pp.1999-2005
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7883
Formation of Thiazole and 1,3-Thiazolidine Sulfoxide from Pyrolysis of a Thiolsulfinate

Heduck Mah, Kee Dal Nam, and Hoh-Gyu Hahn*

*Organic Chemistry Laboratory, Korea Institute of Science and Technology, P.O. Box 131, Cheongryang, Seoul 136-791, Korea

Abstract

The mechanistic study on the prolytic transformation of a thiolsulfinate (2) is described. The reactive intermediates sulfenic acid (6) and thioaldehyde (8) were formed resulting from S-S bond cleavage and a hydrogen transfer from sulfenyl to sulfinyl moiety. A stereospecific cyclization of 6 to cis-sulfoxide (4) was observed, which arouse from the geometrical requirements of a planar transition state for the reacting bonds and atoms in the sigmatropic rearrangement. In the transformation of 8 to thiazole (9), the amide carbonyl group facilitated the elimination of a neighboring proton and enabled to furnish the nucleophilic attack of a thiocarbonyl sulfur at β to internal carbonyl group to yield thiazole (9).