Studies of Azo Colors. XI. The Diazo-coupling Reaction of Pyrroles

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概要

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• Kinetic studies have been made of the coupling reaction of several diazonium salts with pyrrole, <I>N</I>-methylpyrrole, and <I>N</I>-ethoxycarbonylpyrrole. In the case of pyrrole, it was found, from the dependence of the apparent rate constant on the pH values, that the undissociated pyrrole reacted with diazonium salts in the pH range from 4.7 to 8.2, whereas in the pH region higher than 10.0 the reactive species was the conjugate base of pyrrole. The reactivity of the pyrrole anion was higher by a factor of 8 powers of ten than that of the undissociated pyrrole. The effects of the substituents of diazonium salts on the reaction rates were also investigated. The ρ-values (4.3–4.6) obtained in the Hammett plots were practically the same as those of diazo-coupling reactions which involve ordinary aromatic amines as coupling components.

• 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

• Sekiguchi Shizen

  Department of Chemistry, Faculty of Engineering, Gunma University

• Matsui Kohji

  Department of Chemistry, Faculty of Engineering, Gunma University

• Mitsumura Kazuo

  Department of Chemistry, Faculty of Engineering, Gunma University

• Mitsumura Kazuo

  Department of Synthetic Chemistry, Faculty of Engineering, Gunma University

関連論文

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• Solvent Effects in Diazo-coupling Reactions
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• Tris(benzimidazo)-1,3,5-triazine from the Thermolysis of 2-Aryloxybenzimidazoles
• Studies of Azo Colors. VIII. The Azo-coupling Reactions of Active Methylene Compounds
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• Photolyses of azidotriazines in organic nitro compounds.
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• Reactions of Diazomethyl-1,3,5-triazines with Cyclohexane
• The Effect of Acylamino Groups in Diazo-coupling Reactions
• Effects of Substituents on the Smiles Rearrangement of O-s-Triazmyl-2-aminophenoIs
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