Reaction of 1,1,2,2-tetrachloro-2,2a.ALPHA.,4.ALPHA.,8b.ALPHA.-tetrahydrocyclobuta-[c]quinolin-3(1H)-one with nucleophiles; Reaction, product structure, and mechanism.

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概要

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• 2a-Substituted dichlorodihydrocyclobuta[<I>c</I>]quinolin-3(4<I>H</I>)-one (<B>3</B>) and trichlorovinyl-2-quinolone (<B>4</B>) were obtained from the cross photocycloadduct of 2-quinolone and tetrachloroethylene. The position of the substituent on <B>3</B> was determined from the NOE volumes in the NOESY spectrum in comparison with the AM1 geometries. The reaction of the photoadduct (<B>1</B>) with a base or nucleophile, yielding <B>3</B> and/or <B>4</B>, was interpreted to proceed via a cyclobutene intermediate formation followed by an S<SUB>N</SUB>2′ displacement or [2+2] cycloreversion.

• 公益社団法人 日本化学会の論文

著者

• 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

• Hirano Tsuneo

  Department Of Chemistry Faculty Of Science Ochanomizu University

• Hasegawa Masaki

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

• Hasegawa Masaki

  Department of Synthetic Chemistry, Faculty of Engineering, University of Tokyo

• Saigo Kazuhiko

  Department of Applied Chemistry, Faculty of Engineering Saitama University

• Saigo Kazuhiko

  Department of Synthetic Chemistry, Faculty of Engineering, University of Tokyo

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