The stereoisomerization of N,N'-diacyl derivatives of indigo.

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概要

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• The <I>cis</I>-isomers of <I>N</I>,<I>N</I>′-diacylindigo (<I>e.g.</I>, <I>cis</I>-<I>N</I>,<I>N</I>′-diacetyl-, distearoyl-, dibenzoyl-, and bis(3,5-dinitrobenzoyl)-indigo) were found to separate out in a crystalline form from a solution of the corresponding <I>trans</I>-isomer upon irradiation. The kinetics of the <I>cis</I>-to-<I>trans</I> isomerization of these four <I>cis</I>-<I>N</I>,<I>N</I>′-diacylindigos was studied, the relative rates being 7.9, 11.0, 1.0, and 5.1 respectively. Several amines were found to accelerate the <I>cis</I>-to-<I>trans</I> isomerization in the order of: Et<SUB>2</SUB>NH>PrNH<SUB>2</SUB>>Et<SUB>3</SUB>N><I>i</I>-Pr<SUB>2</SUB>NH in the case of <I>cis</I>-<I>N</I>,<I>N</I>′-diacetylindigo and in the order of: Et<SUB>2</SUB>NH><I>i</I>-Pr<SUB>2</SUB>NH>PrNH<SUB>2</SUB>>Et<SUB>3</SUB>N in the case of <I>cis</I>-<I>N</I>,<I>N</I>′-dibenzoylindigo.

• 公益社団法人 日本化学会の論文

著者

• MATSUZAKI Ryuichi

  Department of Physiology, Kansai Medical University

• Nishio Takehiko

  Department Of Chemistry University Of Tsukuba

• Fujiki Kiyoko

  Department of Agricultural Chemistry, Faculty of Agriculture, Meiji University

• Omote Yoshimori

  Department of Chemistry, Faculty of Science, Tokyo Kyoiku University

• Kashima Choji

  Department of Chemistry, The University of Tsukuba

• Imada Satoshi

  Department of Chemistry, University of Tsukuba

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