The photocycloaddition of N-vinylcarbazole with 3-cyanostyrene.
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概要
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The photocycloaddition reaction of <I>N</I>-vinylcarbazole (VCZ) as an electron donor, with 3-cyanostyrene as an electron acceptor, was studied. In nonpolar solvents, two cyclobutanes of <I>cis</I>-1-(9-carbazolyl)-2-(3-cyanophenyl)cyclobutane and <I>trans</I>-1-(9-carbazolyl)-2-(3-cyanophenyl)cyclobutane (in a ratio of 3 : 1) were obtained from an exciplex intermediate. The structure of cis cyclobutane seemed to originate from a sandwich conformation of the exciplex. In polar solvents, a photodissociation to free ion radicals was observed and <I>trans</I>-1,2-di(9-carbazolyl)cyclobutane was produced efficiently by means of a chain mechanism via a cation radical of VCZ. Transient intermediates were measured by means of nanosecond laser photolysis; the results supported the reaction scheme.
- 公益社団法人 日本化学会の論文
著者
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Tsuchida Akira
Department Of Applied Chemistry Gifu University
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Yamamoto Masahide
Department Of Hematology Tokyo Medical And Dental University
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Nishijima Yasunori
Department of Chemistry Polytechnic Institute of Brooklyn
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Tsuchida Akira
Department of Polymer Chemistry, Faculty of Engineering, Kyoto University
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