Studies on the Isomerization of 2,4-Dinitrophenylhydrazones of Some Aliphatic α-Keto Acids and the Preparation of Their Geometrical Isomers

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概要

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• <I>Cis</I>-<I>trans</I> isomerization of 2,4-dinitrophenylhydrazones of some aliphatic α-keto acids takes place in water and some organic solvents by the catalysis of hydrogen ions. <I>Trans</I> isomer is more stable than <I>cis</I> isomer for lower keto acids and the reverse is the case for higher keto acids. The fraction of <I>cis</I> isomer in isomeric mixture at equilibrium in organic solvents such as ethyl acetate and ethyl ether, saturated with 6N hydrochloric acid, was larger than that in aqueous solution. The two isomers could be separated by means of the difference in their solubility characteristics in 1N sodium carbonate except for some keto acids with tertiary or quaternary β-carbon. Melting points of some pairs of the hydrazone isomers were found to be the same when measured by the usual method. This is due to the isomerization of one isomer to the other which takes place during the course of heating.

• 公益社団法人 日本化学会の論文

著者

• Tokushige Masanobu

  Department Of Chemistry Faculty Of Science Kyoto University

• Katsuki Hirohiko

  Department of Chemistry, Faculty of Science, Kyoto University

• Katsuki Hirohiko

  Department Of Chemistry Faculty Of Science Kyoto University

• Tanaka Shozo

  Department of Chemistry, Faculty of Science, Kyoto University

• Tanegashima Chizuko

  Department of Chemistry, Faculty of Science, Kyoto University

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