Studies of Azo Colors. VIII. The Azo-coupling Reactions of Active Methylene Compounds

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概要

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• The kinetics of the azo-coupling reactions of various active methylene compounds with diazobenzene-4-sulfonic acid have been studied spectrophotometrically. In the reactions of all the active methylene compounds used, it was found that the reaction rate was proportional to both the concentration of the diazonium salt and the carbanion (or enolate ion) of the azo component. In the reactions of a series of β-dicarbonyl compounds, a plot of the logarithms of the rate constants against the p<I>K<SUB>a</SUB></I> values of active methylene compounds gave a straight line. However, the correlation between the reactivity and p<I>K<SUB>a</SUB></I> was found unsatisfactory in the case of active methylene compounds with such electron-withdrawing substituents as NO<SUB>2</SUB>, CN, COR, SO<SUB>2</SUB>R, and Cl. These results are discussed in terms of the nucleophilicity of these carbanions.

• 公益社団法人 日本化学会の論文

著者

• Hashida Yoji

  Department of Chemistry, Faculty of Engineering, Gunma University

• Matsui Kohji

  Department of Chemistry, Faculty of Engineering, Gunma University

• Kobayashi Morio

  Department of Synthetic Chemistry, Faculty of Engineering, Gunma University

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