Homoconjugated diene as a dienophile to troponoid compounds: The stereoselective addition reactions of tropone and 8,8-dicyanoheptafulvene with tricyclo(3.2.2.02,4)nona-6,8-diene derivative and thermal and photochemical isomerizations of the adducts.

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概要

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• Thermal addition reactions of tropone and 8,8-dicyanoheptafulvene with a homoconjugated diene, dimethyl 3-cyanotricyclo[3.2.2.0<SUP>2,4</SUP>]nona-6,8-diene-6,7-dicarboxylate derivative, proceeded stereoselectively to give endo-[4+2]-type cycloadducts, where the troponoids acted as 4 π components. Upon photo-irradiation the adducts afforded intramolecular [2+2]-type addition products to verify the endo-form of the adducts. Molecular orbital caluculations suggested that the stereoselectivity could be explained by secondary orbital interactions between the HOMO of the troponoid compounds and the LUMO of the tricyclic compound. A thermal reaction of the adducts gave three-membered ring opened products, which further proceeded through an intramolecular [2+2]-type reaction upon photo-irradiation.

• 公益社団法人 日本化学会の論文

著者

• Ito Kazuaki

  Department Of Applied Chemistry Nagoya Institute Of Technology

• Takahashi Kensuke

  Department Of Applied Chemistry Nagoya Institute Of Technology

• Noro Yukie

  Department Of Applied Chemistry Nagoya Institute Of Technology

• Saito Katsuhiro

  Department Of Agricultural And Resource Economics The University Of Tokyo

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