Photochemical reactions of aromatic compounds. XLII. Photosensitized reactions of some selected diarylcyclobutanes by aromatic nitriles and chloranil. Implications of charge-transfer contributions on exciplex reactivities.

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概要

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• Photosensitized reactions of <I>cis</I>- and <I>trans</I>-1,2-diphenylcyclobutane and <I>cis</I>-<I>transoid</I>-<I>cis</I>-cyclobuta[1,2-<I>a</I> : 4,3-<I>a</I>′]diindene by 1-cyanonaphthalene, 9,10-dicyanoanthrancene, 1,4-dicyanonaphthalene, and chloranil, which mainly give the ring-splitting product (styrene or indene), have been investigated to explore steric and electronic requirements of the reactions associated with charge-transfer and excitation-resonance contributions of exciplex intermediates. The reaction efficiencies increase with an increase in the electron-accepting power of the sensitizers irrespective of the spin states. The formation of 1-phenyltetralin in the photosensitized reactions of the diphenylcyclobutanes occurs from the polar singlet exciplex with the dicyanoarenes but not at all from the less polar exciplex with 1-cyanonaphthalene nor from the triplet chloranil exciplex of high charge-transfer nature. Exciplex reactivities are discussed in terms of roles of charge-transfer contributions in exciplex decay channels as well as in terms of configurational and conformational effects on orbital interactions in the cyclobutanes.

• 公益社団法人 日本化学会の論文

著者

• Sakurai Hiroshi

  Department Of Applied Chemistry Graduate School Of Engineering Hiroshima University

• PAC Chyongjin

  Department of Chemistry, Toho University

• Yanagida Shozo

  Department of Applied Chemistry, Faculty of Engineering, Osaka University

• Ohtsuki Tomohito

  Department of Chemical Process Engineering, Faculty of Engineering, Osaka University

• Shiota Yozo

  Department of Chemical Process Engineering, Faculty of Engineering, Osaka University

• Pac Chyongjin

  Department of Chemical Process Engineering, Faculty of Engineering, Osaka University

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