Homogeneous Electron Exchange in Catalytic Polarographic Reduction.

Lund, Henning; Michel, Marie-Andrée; Simonet, Jacques; Krane, Jostein; Taticchi, A.; Mannervik, Bengt

doi:10.3891/acta.chem.scand.28b-0900

Cited by 60 publications

(26 citation statements)

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“…Usually the first electron transfer between aromatic organic mediators and halogenated compounds is described as a homogeneous electron transfer. [17][18][19] The nature of the mediator should therefore not affect the selectivity of the subsequent chemical reaction taking place. Thus the reaction with anthracene might not be completely outer sphere.…”

Section: Resultsmentioning

confidence: 99%

“…This is in agreement with an outer-sphere electron transfer, as usually described in the literature for this type of reaction. [17][18][19] Direct electrolysis is also reported in the table, and the distribution of dichlorobenzenes does not show any significant difference when compared with the mediated approach. Only a poorer current efficiency is noted in the former.…”

Section: Mediated Electrolysis Of 124-trichlorobenzene-electrolysismentioning

confidence: 99%

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Mediated Approach for the Electrochemical Reduction of Chlorobenzenes in Nonaqueous Media

Guena

Wang

Gattrell

et al. 2000

J. Electrochem. Soc.

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The use of a range of mediators for the partial or complete dechlorination of a series of polychlorinated benzenes has been investigated. The dechlorinations were carried out in acetonitrile, and the products were analyzed by gas chromatography-mass spectroscopy (GC-MS). The partial dechlorination using organic mediators was successful and good control of the reaction (i.e., monodechlorination) and good efficiency could be achieved. Some mediators showed poor current efficiencies due to the lower stability of their anion radical in the presence of protons. The monodechlorination of trichlorobenzene with four different mediators showed that the product distribution in terms of initial chlorine removed was little affected by the mediator used. This product distribution has also been investigated for the whole series of polychlorobenzenes. Polydechlorination using a single mediator was tried using biphenyl, anthracene, and dibenzofuran. After passing enough charge to completely dechlorinate trichlorobenzene, few chlorinated benzenes remained in solution and less than the expected amount of benzene was detected. The was explained by nonvolatile products undetected by GC-MS. It is suggested that when higher overpotential mediators are used, the reaction shifts to produce higher molecular weight products by radical-radical coupling reactions. Biphenyl might be a convenient mediator for the dechlorination of polychlorobenzene or even polychlorobiphenyl.

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Section: Resultsmentioning

confidence: 99%

Section: Mediated Electrolysis Of 124-trichlorobenzene-electrolysismentioning

confidence: 99%

Mediated Approach for the Electrochemical Reduction of Chlorobenzenes in Nonaqueous Media

Guena

Wang

Gattrell

et al. 2000

J. Electrochem. Soc.

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“…[138][139][140][141] Typically an aromatic compound is reduced in an aprotic medium to the radical anion or dianion which transfers an electron to a substrate. On electron uptake the substrate forms a radical ion which undergo a fast, irreversible reaction, usually a cleavage, or it reacts by a dissociative electron transfer to a radical and an anion.…”

Section: Rcoomentioning

confidence: 99%

A Century of Organic Electrochemistry

Lund

2002

J. Electrochem. Soc.

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161

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“…Lund and coworkers [131] pioneered the use of aromatic anion radicals as mediators in a study of the catalytic reduction of bromobenzene by the electrogenerated anion radical of chrysene. Other early investigations involved the catalytic reduction of 1-bromo-and 1-chlorobutane by the anion radicals of trans-stilbene and anthracene [132], of 1-chlorohexane and 6-chloro-1-hexene by the naphthalene anion radical [133], and of 1-chlorooctane by the phenanthrene anion radical [134].…”

Section: Catalytic Reduction Of Carbon-halogen Bondsmentioning

confidence: 99%

Oxidation and Reduction of Halogen‐containing Compounds

Peters

2004

Encyclopedia of Electrochemistry

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The sections in this article are Introduction Anodic Processes Halogenated Alkanes Alicyclic Halides Aryl Halides Cathodic Processes Halogenated Alkanes Halogenated Alkenes and Alkynes Benzyl Halides Alicyclic Halides Aryl Halides Acyl and Phenacyl Halides Aliphatic α‐Halocarbonyl Compounds Halogenated Heterocyclic Compounds Catalytic Reduction of Carbon–Halogen Bonds

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Homogeneous Electron Exchange in Catalytic Polarographic Reduction.

Cited by 60 publications

References 0 publications

Mediated Approach for the Electrochemical Reduction of Chlorobenzenes in Nonaqueous Media

Mediated Approach for the Electrochemical Reduction of Chlorobenzenes in Nonaqueous Media

A Century of Organic Electrochemistry

Oxidation and Reduction of Halogen‐containing Compounds

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