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Paper | Regular issue | Vol 65, No. 6, 2005, pp.1373-1383
Published online, 1st April, 2005
DOI: 10.3987/COM-05-10373
Generation and [2+3] Cycloadditions of a Sulfonylated Thiocarbonyl S-Methanide

Katarzyna Urbaniak, Magdalena Sobieraj, Grzegorz Mloston,* Anthony Linden, and Heinz Heimgartner*

*Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland


The sulfonylated thiocarbonyl S-methanide (2a) was generated in situ by addition of diazomethane to the C-sulfonylated dithioformate (1a) and subsequent thermal elimination of nitrogen. This 1,3-dipole was intercepted by C,C- and C,S-dipolarophiles. Whereas in the first case the cycloadducts (10) and (11) could be isolated as stable products, the cycloadducts of type (8), which are the proposed products of the reaction with thioketones, underwent a spontaneous rearrangement to give open-chain ketene dithioacetals (5) and (6).