Stereoselective [2π+4π]-Type Addition Reactions of Benzocyclobutadiene with 2-Substituted Tropones and 8, 8-Dicyanoheptafulvene

Katsuhiro SAITO; Hiroyuki WATANABE; Kensuke TAKAHASHI

doi:10.1248/cpb.40.2831

Katsuhiro SAITO, Hiroyuki WATANABE, Kensuke TAKAHASHI

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Keywords: 2-substituted tropone, 8, 8-dicyanoheptafulvene, benzocyclobutadiene, [2π+4π]-type cycloaddition, stereoselective

JOURNALS FREE ACCESS

Volume 40 (1992) Issue 10 Pages 2831-2833

DOI https://doi.org/10.1248/cpb.40.2831

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Abstract

Thermal addition reactions of 2-substituted tropones and 8, 8-dicyanoheptafulvene with benzocyclobutadiene proceeded stereoselectively to produce endo-[2π+4π]-type cyclo adducts, where the troponoid compounds acted as 4π components. Molecular orbital calculations were employed to explain the selectivity.

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