A novel type of the photo-addition compound, 5,8,13,14-tetraoxo-5,5a,6, 7,7a,8,13,13a,13b,14-decahydropentaphene derivatives (3), consisting of two molecules of 1,4-naphthoquinone and one molecule of an olefin was obtained in the photochemical reaction of 1,4-naphthoquinone with olefins. Its structure was determined from spectral data as well as results obtained from the chemical reactions. Olefins which give this type of photo-addition compound are characterized by their bicyclo-ring systems containing considerable ring strains. The reaction mechanism for formation of the compound was discussed in terms of the ring strains of olefins and the nature of the photo-excited 1,4-naphthoquinone.
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Maruyama et al. (1975) studied this question.
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