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Paper | Regular issue | Vol 34, No. 12, 1992, pp.2293-2299
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6103
Expected and Unexpected Reactions of N,N-Diphenylhydrazones with Chlorocarbonylsulfenyl Chloride

Chang He Xi and Gert Kollenz*

*Institute of Organic Chemistry, Isotope Department, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria


The N,N-diphenylhydrazones (1) and chlorocarbonylsulfenyl chloride cyclize to give the thiazolones (2), with the benzoyl derivative (1i) the 1,3-oxathiolone (3) is obtained. At low temperatures the hydrazines (1f,g,i), are selectively oxidized affording α-oxohydrazones (4). From all thiazolones (2a,d) only can be rearranged into the indole derivatives (6) via a Fischer-indolizatioin process.