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Communication | Regular issue | Vol 65, No. 7, 2005, pp.1553-1556
Published online, 28th April, 2005
DOI: 10.3987/COM-05-10396
Reaction of 3,3,5,5-Tetramethylthiolane-2,4-dithione with Benzyne: Novel Formation of Benzodithiole

Kentaro Okuma,* Taeko Tsubone, Toshiyuki Shigetomi, Kosei Shioji, and Yoshinobu Yokomori

*Department of Chemistry, Faculty of Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan


Reaction of 3,3,5,5-tetramethylthiolane-2,4-thione with benzyne gave a new type of benzodithiole in 78% yield. Dithioester’s thiocarbonyl group initially attacked benzyne to afford the corresponding betaine, which finally rearranged to give benzodithiole. On the other hand, reaction of cyclic dithiolactone with benzyne recovered the starting dithiolactone in almost quantitatively.