Abstract
Abstract Thermal addition reactions of tropone and 8,8-dicyanoheptafulvene with a homoconjugated diene, dimethyl 3-cyanotricyclo[3.2.2.02,4]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.
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