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Paper | Regular issue | Vol 51, No. 1, 1999, pp.61-66
Published online, 1st January, 1970
DOI: 10.3987/COM-98-8335
Regioselective Synthesis of 1H-2-Benzoselenopyrans. Reaction of 4,4'-Dimethoxyselenobenzophenone with Acetylenes

Kentaro Okuma,* Yuji Koga, Yayoi Furunushi, Kazuki Kojima, and Kosei Shioji

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

Abstract

4,4’-Dimethoxyselenobenzophenone combines as a diene with methyl propiolate, ethyl propiolate, and phenylacetylene producing 1H-2-benzoselenopyrans; the primary [4+2] cycloaddition is followed by 1,3-prototropy. This reaction proceeds regioselectively. On the other hand, a nonaromatic ketone was obtained by using propiolic acid as the substrate.