The reaction of nitrile oxides with alkyl- and alkyl-halo-substituted p-benzoquinones.

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概要

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• Various aromatic nitrile <I>N</I>-oxides, sterically stabilized and unstabilized ones, were allowed to react with several alkyl- and alkyl-halo-substituted <I>p</I>-benzoquinones with a view to studying the influence of quinone substituents on the mode of the addition reaction. Mono-, di-, and tri-substituted quinones with such substituents gave isoxazoline derivatives formed through addition of nitrile oxides to the C=C bond of the quinones. 2-Chloro-5- and -6-methyl-<I>p</I>-benzoquinones gave two kinds of C=C adducts, one formed through the addition to the C=C of methyl-substituted side and the other to that of chlorine-substituted side, and the latter adducts were not isolable due to the prompt dehydrochlorination forming the fully-conjugated isoxazoloquinones and subsequent C=O addition of another nitrile <I>N</I>-oxide forming spirodioxazole derivatives.

• 公益社団法人 日本化学会の論文

著者

• Shiraishi Shinsaku

  Institute Of Industrial Science The University Of Tokyo

• Imamura Kiyoshi

  Institute of Industrial Science, The University of Tokyo

• Holla B.

  Institute of Industrial Science, The University of Tokyo

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