Mah, H Nam, KD Hahn, HG 2024-01-21T18:02:13Z 2024-01-21T18:02:13Z 2021-09-05 1997-10-01 0385-5414 https://pubs.kist.re.kr/handle/201004/143553 The mechanistic study on the pyrolytic 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 beta to internal carbonyl group to yield thiazole (9). English PERGAMON-ELSEVIER SCIENCE LTD THIOALDEHYDES GENERATION Formation of thiazole and 1,3-thiazolidine sulfoxide from pyrolysis of a thiolsulfinate Article 1 HETEROCYCLES, v.45, no.10, pp.1999 - 2005 HETEROCYCLES 45 10 1999 2005 scie scopus A1997YF18000019 2-s2.0-0001395889 Chemistry, Organic Chemistry Article THIOALDEHYDES GENERATION thiolsulfinate