Photochemical reactions of aromatic compounds. XXXIII. Photoreactions of 1-cyanonaphthalene with indene in various solvents.

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概要

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• The stereospecific photocycloaddition of 1-cyanonaphthalene to indene occured in cyclohexane, benzene, diethyl ether, tetrahydrofuran, and ethyl acetate, giving the <I>endo</I> head-to-head cycloadduct as the sole 1:1-adduct. The mechanism was discussed in terms of the exciplex intermediacy. In methanol or in acetonitrile in the presence of water, the photoreaction gave the dihydrocycloadduct (<B>8</B>), accompanied by the formation of 2-methoxyindan and 2,2′-dimethoxy-1,1′-biindanyl or 2-indanol and 1-hydroxy-2,2′-biindanyl. In these solvents, the reactions were suggested to be initiated by photochemical electron transfer; the methoxylated or hydroxylated compounds are formed by the nucleophilic attack of methanol or water on the indene cation. Anionic species, including the 1-cyanonaphthalene anion, were suggested to play important roles in the formation of <B>8</B>.

• 公益社団法人 日本化学会の論文

著者

• SAKURAI Hiroshi

  The Institute of Scientific and Industrial Research, Osaka University

• Pac Chyongjin

  The Institute of Scientific and Industrial Research, Osaka University

• Yasuda Masahide

  The Institute of Scientific and Industrial Research, Osaka University

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