The Ullmann condensation reaction of haloanthraquinone derivatives with amines in aprotic solvents. VI. The combination of Cu(I) and hydroxo or alkoxo Cu(II) as effective catalyst system.
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概要
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The reaction rate of the Ullmann condensation reaction of haloanthraquinone with ethylenediamine (EN) by copper(I) halide catalyst decreased along with the formation of inactive Cu(II) species [Cu(EN)<SUB>2</SUB>X<SUB>2</SUB>] by one-electron transfer from Cu(I) to haloanthraquinone. However, the combination of Cu(I) and Cu(II) salts, having an OH, OCH<SUB>3</SUB>, or OCOR group, enhanced the reaction rate in the following order: CuCl<CuCl–CuCl(OCH<SUB>3</SUB>)<CuCl–Cu(OCH<SUB>3</SUB>)<SUB>2</SUB><CuCl–Cu(OH)<SUB>2</SUB>. In condensation using Cu(OR)<SUB>2</SUB> or CuCl(OCH<SUB>3</SUB>) alone, the Cu(II) species was reduced to Cu(I) to form an active catalyst system [Cu(I)+Cu(II)]. On the other hand, CuBr<SUB>2</SUB> or CuCl<SUB>2</SUB> was not reduced and was ineffective for the reaction. These were confirmed by ESR measurements and the presence of a dehalogenation product. Mixed valence species bridged by the alkoxo or hydroxo group was proposed as an active species.
- 公益社団法人 日本化学会の論文
著者
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Arai Sadao
Department Of Chemistry Tokyo Medical University
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Yamagishi Takamichi
Department Of Applied Chemistry Graduate School Of Engineering Tokyo Metropolitan University
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Hashimoto Yoshio
Department Of Anesthesiology University Of Hirosaki School Of Medicine
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Hida Mitsuhiko
Department of Industrial Chemistry, Faculty of Technology, Tokyo Metropolitan University
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