The Ullmann condensation reaction of haloanthraquinone derivatives with amines in aprotic solvents. III. The formation and role of copper(II) species in the condensation with 2-aminoethanol by copper(I) catalyst.

スポンサーリンク

概要

• 論文の詳細を見る

• The ESR spectra of the Ullmann condensation reaction system of 1-bromoanthraquinone-2-aminoethanol-CuBr showed that copper(II) species and 1-bromoanthraquinone radical anion were formed by an electron transfer from copper(I) species to 1-bromoanthraquinone. Although copper(II) species alone had little catalytic activity, the resulting copper(II) species increased the catalytic activity of the copper(I) species, and a pseudo-first order rate constant could be expressed as follows: <I>k</I>=<I>k</I><SUB>1</SUB>[Cu<SUP>I</SUP>]+<I>k</I><SUB>2</SUB>[Cu<SUP>I</SUP>][Cu<SUP>II</SUP>]. According to the magnitude of <I>k</I><SUB>1</SUB> and <I>k</I><SUB>2</SUB><I>C</I><SUB>0</SUB>, where <I>C</I><SUB>0</SUB> is the initial concentration of copper(I) catalyst, the reaction of haloanthraquinone with 2-aminoethanol by copper(I) catalyst can be classified into three modes. When <I>k</I><SUB>1</SUB><<I>k</I><SUB>2</SUB><I>C</I><SUB>0</SUB>, an induction period is present. The possible mechanisms of the cooperation between copper(I) and copper(II) species have been proposed. It has been also found that 1-bromoanthraquinone radical anion was responsible for the debromination.

• 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

• Hida Mitsuhiko

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

• Hida Mitsuhiko

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

関連論文

• Metabolism of Pyrogallol to Purpurogallin by Human Erythrocytic Hemoglobin
• Molecular Structure of 1, 3-Disubstituted π-Allyl Palladium (II) Complecxes with a Chiral Diphosphine : The Intermediate of Palladium-catalyzed Asymmetric Asymmetric Allylic Alkylation
• Isomerization of Imines Catalyzed by Ruthenium-Hydride Complexes
• Organogel Formation by Self-assembly of Ag(I) and Mono-urea Derivatives Containing Pyridyl Group
• Phenoxazine Compounds Produced by the Reactions with Bovine Hemoglobin Show Antimicrobial Activity Against Non-tuberculosis Mycobacteria
• Immediate-type hypersensitivity to pyridoxal 5'-phosphate: Study of in vivo and in vitro cross-reactivity and identification of the antigenic determinant
• Quantitative Determination of Sugars and Myo-Inositol in Citrus Fruits Grown in Japan Using High-Performance Anion-Exchange Chromatography
• Effective Catalysts for Transfer Hydrogenation of Ketones and Imines by Propan-2-ol : Ruthenium-Hydride or Ruthenium-Dihydride Complexes
• Syntheses of Ruthenium(II) Complexes with Pentadentate Ligands and Catalytic Oxidation of Alkane Using 2,6-Dichloropyridine N-Oxide
• ピレンおよびベリレンπ-ラジカルカチオンへの求核置換反応によるピリジウム共役組織体の電解合成
• Facile Chemical Dehydrogenation of α-Amino Acids Chelated to a Ruthenium(II) Ion:(α-Imino acidato)bis(1, 10-phenanthroline)ruthenium(II) Complexes^
• Syntheses and Characterization of Chloro(Me_2SO)ruthenium(II) Complexes with Tris(2-pyridylmethyl)amine of N, N-Bis(2-pyridylmethyl)glycinate and Their Application for Catalytic Hydroxylation of Alkane
• Kinetic studies on the amination of leucoquinizarin.
• Ullmann condensation reaction of haloanthraquinone derivatives with amines in aprotic solvents.
• The Ullmann condensation reaction of haloanthraquinone derivatives with amines in aprotic solvents. II. The presence of an induction period in the condensation with 2-aminoethanol.
• Asymmetric hydrogenation of .ALPHA.-keto acid derivatives with Rh(I)-chiral diphosphinite system. Effect of halide counterion on the asymmetric induction.
• Photoreduction of aminoanthraquinones by an electron transfer via the upper excited n.PI.* triplet state.
• 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.
• Synthesis of Naphth(1,2,3-cd)indol-6(2H)-one Derivatives and Their Fluorescence Properties.
• Synthesis of Azonia Derivatives of Benzoperylene and Benzocoronene by Photocyclization.
• The Ullmann condensation reaction of haloanthraquinone derivatives with amines in aprotic solvents. III. The formation and role of copper(II) species in the condensation with 2-aminoethanol by copper(I) catalyst.
• Amide ion formation and N-alkylation of aminoanthraquinones in the presence of potassium hydroxide in dimethyl sulfoxide.
• Synthesis of 2,6-dihydronaphth(1,2,3-cd)indol-6-ones.
• 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.
• The Ullmann condensation reaction of haloanthraquinone derivatives with amines in aprotic solvents. IV. Kinetic studies of the condensation with ethylenediamine.
• Solvent effects on the photoamination of 1-amino-2,4-dibromoanthraquinone. I. Photoamination in benzene via intramolecular charge transfer excited triplet state.
• Solvent effects on the photoamination of 1-amino-2,4-dibromoanthraquinone. II. Dual mode of the photoamination in ethanol via the S1(1CT) and T1(3CT) states.
• The Nucleophilic Photo-substitution Reaction of Anthraquinone Derivatives. I. The Photo-amination of Sodium 1-Amino-4-bromoanthraquinone-2-sulfonate
• Studies of the Aggregation of Dyes. The Scope of Application of the Maximum-slope Method
• Effects of solvent and temperature on the 1,4-asymmetric induction in the diastereoselective hydrogenation of dehydrodipeptides.
• Mechanism of the Ullmann Condensation. I. Kinetic and Thermodynamic Studies
• Asymmetric hydrogenation of dehydroamino acids and dehydrodipeptides with rhodium(I)-modified DIOP catalysts.
• The Electrochemical Behavior of the Low-valent Transition Metal Complexes. II. Iron(0)-2,2′-Bipyridine Complexes
• Photochemical electron transport from water layer to organic layer via sodium anthraquinone-2-sulfonate by stepwise two photon excitation.
• The Electrochemical Behavior of the Low-valent Transititon-metal Complexes. I. Nickel-2,2′-Dipyridyl Complexes.
• The molecular structure of (+)589-.BETA.2-(3-methyl-2-iminobutanoato)((2S,10S)-4,8-diazaundecane-2,10-diamine)cobalt(III) perchlorate: .ALPHA.-Imino acidato complex.

もっと見る 閉じる

スポンサーリンク