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■ Novel Reaction Course of Thiiranes to Vinyloxiranes: Reaction of Benzyne with Thiiranes and Aldehydes

Kentaro Okuma,* Yuxuan Qu, and Noriyoshi Nagahora

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

Abstract

Reaction of 2 molar amount of 2-(trimethylsilyl)phenyl triflate with thiiranes and aldehydes in the presence of CsF afforded vinyloxiranes in one-pot operation. Reaction of benzyne with thiiranes gave the corresponding alkenyl phenyl sulfides, which further reacted with another molar of benzyne to afford sulfonium ylide intermediates. Further treatment of aldehydes gave the corresponding vinyloxiranes.