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Communication | Regular issue | Vol 43, No. 3, 1996, pp.527-530
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7350
Cycloadditions of 1,5- and 1,7-Azulenequinones to Benzo[c]furan and Its 1,3-Diphenyl Derivative

Hitoshi Takeshita*, Yong Zhe Yan, Akira Mori, and Tetsuo Nozoe*

*Institute of Advanced Material Study, 86, Kyushu University, Kasuga-koen, Kasuga, Fukuoka 816, Japan

Abstract

With 1,3-diphenylbenzo[c]furan (DIBF), 1,5-azulenequinone (5-AQ) gave a [2+4] cycloadduct and a [2+4]-[6+4] cycloadduct which were interconverted under mild conditions. This is the first observation of conjugated rearrangement of [2+4] mode to [6+4] mode with the second attack of cycloaddend or conjugated cycloreversion with the rearrangement. 1,7-Azulenequinone (7-AQ) formed two stereoisomeric 1:2-[2+4]-[6+4] cycloadducts. With benzo[c]furan, 5-AQ and 7-AQ afforded two and four stereoisomeric [2+4]-[6+4] cycloadducts, respectively.