Electrocatalytic reduction of some imino compounds on a glassy carbon electrode electrochemically modified with a new copper-salen complex

Azzem, M. Abdel; Mohamed, Ziyaad; Fahmy, H. M.

doi:10.1016/0022-0728(95)04131-1

Cited by 7 publications

(2 citation statements)

References 32 publications

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“…14 In contrast, the information concerning the copper-mediated reduction of imines to amines is very scarce and seems to be limited to some electrocatalytic methods. 15 We want to present herein a simple alternative methodology to those previously described, to effect the reduction of carbonyl compounds and imines under very mild reaction conditions, based by the use of active copper, generated from commercially available copper(II) chloride dihydrate, lithium, and a catalytic amount of DTBB (4,4′di-tert-butylbiphenyl).…”

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confidence: 99%

Reduction of Carbonyl Compounds and Imines Using the CuCl₂·2H₂O-Li-DTBB (Cat.) Combination

Alonso¹,

Vitale²,

Radivoy³

et al. 2003

Synthesis

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The reaction of different carbonyl compounds and imines with a mixture of copper(II) chloride dihydrate, an excess of lithium sand, and a catalytic amount of 4,4′-di-tert-butylbiphenyl (DTBB, 5 mol%) in THF at room temperature, led to the formation of the corresponding alcohols and amines, respectively. The process was also applied to the transformation of α,β-unsaturated carbonyl compounds into the corresponding saturated alcohols. The use of the deuterated copper salt CuCl 2 ⋅2D 2 O allowed the preparation of the corresponding deuterated products.

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confidence: 99%

Reduction of Carbonyl Compounds and Imines Using the CuCl₂·2H₂O-Li-DTBB (Cat.) Combination

Alonso¹,

Vitale²,

Radivoy³

et al. 2003

Synthesis

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“…[2][3][4][5][6][7][8][9] Another strategy to prepare modified electrodes with redox polymer films is to deposit polymer films having the ability to fix the redox species from solution via electrostatic attraction or complexation. [10][11][12][13][14][15][16] Polymeric films of Cu(II), Co(II) complexes of Schiff bases were prepared by Abdel-Azzem et al 17,18 and tested for electrocatalytic reduction of some imino compounds. In searching for new monomer candidates for preparation of modified electrodes, Schiff bases containing free aromatic amine moiety for polymerization seem to be promising for electrodeposition of electroactive polymer films with the ability to fix metal cations via complexation in the present study.…”

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confidence: 99%

Electroactive Polymer Films Formed from the Schiff Base Product of 1,8-Diaminonaphthalene and Dehydroacetic Acid. I. Preparation and Characterization

El-Rahman

Hathoot

El‐Bagoury

et al. 2000

J. Electrochem. Soc.

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Modification of conventional electrodes by coating the surface with polymer films containing redox sites is of interest in electrocatalysis, 1 and many transition metal complexes have been electropolymerized for such purposes. [2][3][4][5][6][7][8][9] Another strategy to prepare modified electrodes with redox polymer films is to deposit polymer films having the ability to fix the redox species from solution via electrostatic attraction or complexation. [10][11][12][13][14][15][16] Polymeric films of Cu(II), Co(II) complexes of Schiff bases were prepared by Abdel-Azzem et al. 17,18 and tested for electrocatalytic reduction of some imino compounds. In searching for new monomer candidates for preparation of modified electrodes, Schiff bases containing free aromatic amine moiety for polymerization seem to be promising for electrodeposition of electroactive polymer films with the ability to fix metal cations via complexation in the present study. The Schiff base obtained by the condensation reaction between 1,8-diaminonaphthalene and dehydroacetic acid, namely, 8-(3-acetylimino-6-methyl-2,4-dioxopyran)-1-aminonaphthalene (AMDAN), according to Scheme 1, was anodically polymerized. The resulting electroactive polymer films were characterized by elemental analysis, thin-layer chromatography, IR, proton nuclear magnetic resonance ( 1 H NMR), and 13 C NMR. ExperimentalThe chemicals lithium perchlorate, 1,8-diaminonaphthalene, dehydroacetic acid, acetonitrile, perchloric and sulfuric acids, and pyridine were analytical grade chemicals (Aldrich) and used without further purification. Aqueous solutions were prepared from bidistilled water. Electrochemical measurements were performed using the EG&G PAR computer measuring system (model 250) and a Hewlett-Packard X-Y recorder (model 7440). A three-electrode electrolytic cell (Bioanalytical system, model C-1A) with a platinum disk electrode (3.0 mm diam) was used as working electrode, a plat-inum sheet (area 2 cm 2 ) as counter electrode, and a Ag/AgCl reference electrode.Schiff base AMDAN (80% yield) was prepared according to the recommended method 19 by the condensation reaction between 1 mol 1,8-diaminonaphthalene and 1 mol dehydroacetic acid. The dehydroacetic acid in ethanol was added dropwise with stirring to hot 1,8-diaminonaphthalene in ethanol. The resulting Schiff base 20 was recrystallized twice from ethanol as faint brown granules, melting point 218ЊC. The structure of Schiff base AMDAN was confirmed by IR, 1 H NMR, 13 C NMR, and elemental analyses. IR spectra were recorded on a Gemini 2000 MHz spectrophotometer in deuterated dimethyl sulfoxide (DMSO), and 13 C NMR spectra were recorded on a Bruker AC-200 E spectrometer. Chemical shifts are reported as ␦ in ppm referenced to external tetramethylsilane (TMS).IR absorption spectra of Schiff base AMDAN give peaks at 3400 cm Ϫ1 corresponding to NH 2 group, 1680, 1690 cm Ϫ1 corresponds to keto and ester groups, respectively, 1640-1600 cm Ϫ1 corresponds to CϭC, 1650 cm Ϫ1 due to CϭN. 1 H NMR (DMSO-d 6 ):

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Electropolymerized Metalloporphyrin Metallophthalocyanine and Metal Schiff Base Complex Films: Applications to Biomimetic Electrocatalysis and Bioelectroanalysis

Pailleret

Bédioui

N4-Macrocyclic Metal Complexes

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Electrocatalytic reduction of some imino compounds on a glassy carbon electrode electrochemically modified with a new copper-salen complex

Cited by 7 publications

References 32 publications

Reduction of Carbonyl Compounds and Imines Using the CuCl₂·2H₂O-Li-DTBB (Cat.) Combination

Reduction of Carbonyl Compounds and Imines Using the CuCl₂·2H₂O-Li-DTBB (Cat.) Combination

Electroactive Polymer Films Formed from the Schiff Base Product of 1,8-Diaminonaphthalene and Dehydroacetic Acid. I. Preparation and Characterization

Electropolymerized Metalloporphyrin Metallophthalocyanine and Metal Schiff Base Complex Films: Applications to Biomimetic Electrocatalysis and Bioelectroanalysis

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Electrocatalytic reduction of some imino compounds on a glassy carbon electrode electrochemically modified with a new copper-salen complex

Cited by 7 publications

References 32 publications

Reduction of Carbonyl Compounds and Imines Using the CuCl2·2H2O-Li-DTBB (Cat.) Combination

Reduction of Carbonyl Compounds and Imines Using the CuCl2·2H2O-Li-DTBB (Cat.) Combination

Electroactive Polymer Films Formed from the Schiff Base Product of 1,8-Diaminonaphthalene and Dehydroacetic Acid. I. Preparation and Characterization

Electropolymerized Metalloporphyrin Metallophthalocyanine and Metal Schiff Base Complex Films: Applications to Biomimetic Electrocatalysis and Bioelectroanalysis

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Reduction of Carbonyl Compounds and Imines Using the CuCl₂·2H₂O-Li-DTBB (Cat.) Combination

Reduction of Carbonyl Compounds and Imines Using the CuCl₂·2H₂O-Li-DTBB (Cat.) Combination