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Communication | Regular issue | Vol 20, No. 10, 1983, pp.1903-1906
Published online, 1st January, 1970
DOI: 10.3987/R-1983-10-1903
Double Sulfer Transfer and 1,2,3-Trithiolane Formation in the Photolysis of a Mesoionic 5-Acetyl-4-thiazolone

Tuvia Sheradsky and David Zbaida

*Department of Organic Chemistry, The Hebrew University of Jerusalem, Jerusalem 91904, Israel


The photolysis of anhydro-5-acetyl-2,3-diphenylthiazolium hydroxide (1a) in alcohols yielded alkyl 2-acetyl-3-anilinocinnamates (3) and 1-acetyl-5,6-diphenyl-6-aza-2,3,4-trithiabicyclo[3.2.0]heptan-7-one (4), in a ratio of 2.6:1. A mechanism which involves two consecutive transfers of sulfur atoms between radical intermediates is suggested.