The Ullmann condensation reaction of haloanthraquinone derivatives with amines in aprotic solvents. V. The formation of active catalyst by the partial oxidation of copper(I) with molecular oxygen.

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概要

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• Although copper(I) is a more effective catalyst than copper(II) in the Ullmann condensation reaction of haloanthraquinones with ethylenediamine in aprotic solvents under a nitrogen atmosphere, the oxidation products of copper(I) by molecular oxygen enhanced the reaction rate compared to copper(I) catalyst. From the studies on the effect of Cu(II) salt addition to Cu(I) salt, solvent effects, and ESR spectra, it was concluded that alkoxycopper(II) species, formed by the oxidation of Cu(I) with molecular oxygen in alcohol–ethylenediamine solution, acted cooperatively with Cu(I) to increase the catalytic activity. The idea was also supported by the fact that the condensation was remarkably accelerated by the combination of Cu(I) and chloromethoxycopper(II). Reaction pathways including the alkoxo and halogen bridged Cu(I)···Cu(II) mixed valence complex are proposed and discussed.

• 公益社団法人 日本化学会の論文

著者

• Arai Sadao

  Department Of Chemistry Tokyo Medical University

• Yamagishi Takamichi

  Department Of Applied Chemistry Graduate School Of Engineering Tokyo Metropolitan University

• Hashimoto Yoshio

  Department Of Anesthesiology University Of Hirosaki School Of Medicine

• Hida Mitsuhiko

  Department of Industrial Chemistry, Faculty of Technology, Tokyo Metropolitan University

• Takayama Nobuo

  Department of Industrial Chemistry, Faculty of Technology, Tokyo Metropolitan University

• Hida Mitsuhiko

  Department of Industrial Chemistry, Faculty of Engineering, Tokyo Metropolitan University

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