Superjacent and subjacent orbitals participations for kinetically-controlled cycloaddition reactions of 2H-cyclohepta[b]furan-2-ones and 8,8-dicyanoheptafulvene to 2,3-bis(methoxycarbonyl)-7-oxabicyclo[2.2.1]heptadiene.

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概要

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• Thermal cycloaddition reactions of 2,3-bis(methoxycarbonyl)-7-oxabicyclo[2.2.1]heptadiene with 2<I>H</I>-cyclohepta[<I>b</I>]furan-2-ones and 8,8-dicyanoheptafulvene gave [4+2]adducts exclusively. This mode is different from the reported [8+2]adduct formations for 2<I>H</I>-cyclohepta[<I>b</I>]furan-2-ones with enamines and alkoxyethenes. A consideration of the superjacent and subjacent orbitals effects of the MO calculations gave a better result in favor of [4+2]adduct formation. Thermolysis of cycloadducts gave the methylene derivatives of homobarrelenes.

• 公益社団法人 日本化学会の論文

著者

• Takeshita Hitoshi

  Institute Of Advanced Material Study 86 Kyushu University

• Mori Akira

  Institute For Materials Chemistry And Engineering Kyushu University

• Tian Guan

  Institute of Advanced Material Study, 86, Kyushu University

• Sugiyama Shigeru

  Institute of Advanced Material Study, 86, Kyushu University

• Yamaguchi Hiroyuki

  College of Technology, Ibaraki University

• Higashi Miwako

  College of Technology, Ibaraki University

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