THE ELECTROHYDROGENATION OF 2-IODONITROBENZENE AT MERCURY AND RANEY METAL-ELECTRODES IN AQUEOUS-METHANOL

被引：11

作者：

COTE, BJ ^{[1
]}

DESPRES, D ^{[1
]}

LABRECQUE, R ^{[1
]}

LAMOTHE, J ^{[1
]}

CHAPUZET, JM ^{[1
]}

LESSARD, J ^{[1
]}

机构：

[1] UNIV SHERBROOKE,ELECTROCHIM ORGAN LAB,SHERBROOKE J1K 2R1,QUEBEC,CANADA

来源：

JOURNAL OF ELECTROANALYTICAL CHEMISTRY | 1993年 / 355卷 / 1-2期

关键词：

D O I：

10.1016/0022-0728(93)80364-N

中图分类号：

O65 [分析化学];

学科分类号：

070302 ; 081704 ;

摘要：

The electrohydrogenation of 2-iodonitrobenzene at mercury and Raney metal electrodes (R-Ni, R-Co and D-Cu) was studied in aqueous methanolic solutions. Four different media were used: a basic KOH medium (pH > 13), a neutral acetate buffered medium (pH 7) and two media containing a pyridine buffer (pH 3 and pH 10). Cyclic voltammetric reductions were carried out at mercury, bright nickel and bright copper cathodes. The product distribution of preparative-scale electrolyses at a mercury pool cathode was compared with that of electrohydrogenation at Raney metal electrodes and of catalytic hydrogenation (open-circuit experiments) at Raney metals. Electrohydrogenation at R-Co and D-Cu electrodes gave 2-iodoaniline with high selectivity (greater-than-or-equal-to 94%). The results are discussed in the light of the various mechanistic pathways.

引用

页码：219 / 233

页数：15

共 26 条

[1]

Adams R. N., 1964, J ELECTROANAL CHEM, V8, P151

[2]

AUGSTINE RL, 1965, CATALYTIC HYDROGENAT, P128

[3] ELECTROCATALYTIC HYDROGENATION OF ORGANIC-COMPOUNDS ON DEVARDA COPPER AND RANEY-NICKEL ELECTRODES IN BASIC-MEDIA [J].

BELOT, G ;

DESJARDINS, S ;

LESSARD, J .

TETRAHEDRON LETTERS, 1984, 25 (47) :5347-5350

[4] INFLUENCE OF THE ADSORPTION OF ORGANIC-COMPOUNDS ON THE KINETICS OF THE HYDROGEN EVOLUTION REACTION ON NI AND NI-ZN ALLOY ELECTRODES [J].

CHEN, LL ;

LASIA, A .

JOURNAL OF THE ELECTROCHEMICAL SOCIETY, 1992, 139 (04) :1058-1064

[5] ELECTROCHEMICAL-BEHAVIOR OF NITROBENZENE AND PHENYLHYDROXYLAMINE ON COPPER ROTATING-DISK ELECTRODES [J].

CYR, A ;

LAVIRON, E ;

LESSARD, J .

JOURNAL OF ELECTROANALYTICAL CHEMISTRY, 1989, 263 (01) :69-78

[6] THE EFFICIENT ELECTROCHEMICAL REDUCTION OF NITROBENZENE AND AZOXYBENZENE TO ANILINE IN NEUTRAL AND BASIC AQUEOUS METHANOLIC SOLUTIONS AT DEVARDA COPPER AND RANEY-NICKEL ELECTRODES - ELECTROCATALYTIC HYDROGENOLYSIS OF N-O AND N-N BONDS [J].

CYR, A ;

HUOT, P ;

BELOT, G ;

LESSARD, J .

ELECTROCHIMICA ACTA, 1990, 35 (01) :147-152

[7] STERIC EFFECTS IN DECOMPOSITION OF HALOGENATED NITROBENZENE ANION RADICALS [J].

DANEN, WC ;

KENSLER, TT ;

LAWLESS, JG ;

MARCUS, MF ;

HAWLEY, MD .

JOURNAL OF PHYSICAL CHEMISTRY, 1969, 73 (12) :4389-&

[8]

DELAIR P, 1991, ELECTROORGANIC SYNTHESIS, P129

[9]

GERGELY T, 1951, J CHEM SOC, P3502

[10]

Haber F., 1898, Z ELEKTROCHEM, V4, P506, DOI 10.1002/bbpc.18980042204

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