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Paper | Regular issue | Vol 45, No. 7, 1997, pp.1281-1288
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7797
Reaction of Thiobenzophenones with Norbornadiene: Unusual Formation of a Seven-membered Cyclic Sulfide

Kentaro Okuma,* Kyoko Shiki, Takafumi Shirokawa, Kazuki Kojima, and Kosei Shioji

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

Abstract

Reaction of thiobenzophenone with 2,5-norbornadiene afforded an unusual seven-membered cyclic sulfide whereas 4,4’-dimethoxythiobenzophenone reacted with 2,5-norbornadiene to afford the corresponding quinone derivative via [4+2] type cycloaddition reaction. The mechanisms of these reactions are discussed.