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Communication | Regular issue | Vol 68, No. 11, 2006, pp.2243-2246
Published online, 8th September, 2006
DOI: 10.3987/COM-06-10849
Novel Formation of 1,2-Dithiolane-3-thione from β-Dithiolactone

Toshiyuki Shigetomi, Akiko Nojima, Kosei Shioji, Kentaro Okuma,* and Yoshinobu Yokomori

*Department of Chemistry, Faculty of Science, Fukuoka University, Jonan-ku, Fukuoka 814-0180, Japan

Abstract

The sulfurization of β-dithiolactone gave 1,2-dithiolane-3-thione via an ionic intermediate. The reaction of 1,2-dithiolane-3-thione with acetylenedicarboxylate esters gave the corresponding spirocyclic 1,3-dithioles in good yields, whereas the reaction of 5-methyl-1,2-dithiole-3-thione with DMAD afforded a 1:2 cycloadduct in 78% yield.