Cycloaddition reactions of heteroaromatic thioketones with maleic anhydride, norbornene, acrylonitrile, styrene, and 2-chloroacrylonitrile.

H Ohmura, S Motoki

Index: Ohmura, Haruo; Motoki, Shinichi Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 4 p. 1131 - 1137

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Citation Number: 12

Abstract

Heteroaromatic thioketones react with maleic anhydride, norbornene, acrylonitrile, and styrene to form the Diels-Alder adducts, respectively. The thioketones also undergo cycloaddition with 2-chloroacrylonitrile followed by elimination of hydrogen chloride to give heteroaromatic analogues of o-quinodimethan derivatives. In these reactions, the thioketones act as a heterodiene on the dienophiles to give [4+ 2] cycloadducts ...