Synthesis of dichlorocyclobuta[b]benzofuran-2a-carboxylic derivatives and 3-(trichloroethenyl)coumarin through cross photocycloadduct of coumarin and tetrachloroethylene.

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概要

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• Photoirradiation of coumarin and tetrachloroethylene with a high-pressure mercury lamp through Pyrex filter in the presence of benzene and benzophenone gave cross cycloadduct (<B>3</B>) in a moderate yield. By treatment with bases or nucleophiles at room temperature, <B>3</B> underwent ring-contraction reaction through lactone-opening, cyclobutene formation, and intramolecular S<SUB>N</SUB>2′ displacement to yield dichlorocyclobuta[<I>b</I>]benzofurancarboxylic derivatives exclusively. By use of a non-nucleophilic base, 3-(trichloroethenyl)coumarin was alternatively obtained through [2+2] cycloreversion of cyclobutene intermediate in a good yield.

• 公益社団法人 日本化学会の論文

著者

• Iitaka Yoichi

  Faculty Of Medicine Teikyo University

• Nonoyama Shinji

  Department Of Crystalline Materials Science Nagoya University

• Yonezawa Noriyuki

  Department Of Chemistry Gunma University

• Saigo Kazuhiko

  Department Of Chemistry And Biotechnology Faculty Of Engineering The University Of Tokyo

• Hasegawa Masaki

  Department Of Materials Science And Technology Faculty Of Engineering Toin University Of Yokohama

• Iitaka Yoichi

  Faculty of Pharmaceutical Science, The University of Tokyo

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