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Paper | Regular issue | Vol 75, No. 6, 2008, pp.1417-1424
Published online, 22nd February, 2008
DOI: 10.3987/COM-07-11321
Reaction of Dithiolactones with Benzyne: A Novel Synthesis of Benzo-1,3-dithioles

Kentaro Okuma,* Akiko Nojima, and Yoshinobu Yokomori

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

Abstract

The reaction of benzyne with several kinds of dithiolactones, such as β-dithiolactone (9), benzothiophene-1-thione (13), 1,2-dithiolane-3-thione (20), and 3,3,5,5-tetramethyl-4-thioxothiolane-2-thione (7), afforded benzo-1,3-dithioles in moderate to good yields, whereas the reaction of benzyne with γ-thionolactone (16) gave γ-lactone and diphenyl disulfide.