Catalytic reduction of ethyl chloroacetate by cobalt(I) salen electrogenerated at vitreous carbon cathodes

Klein, Lee J.; Alleman, Kent S.; Peters, Dennis G.; Karty, Jonathan A.; Reilly, James P.

doi:10.1016/s0022-0728(99)00473-8

Cited by 61 publications

(69 citation statements)

References 30 publications

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“…Therefore, telomers could be produced via reactions of 3 or 4 with solvent-derived radicals, although no supporting experimental evidence has yet been acquired. In addition, prior work in our laboratory involving the reduction of ethyl chloroacetate [22] has revealed that base-promoted elimination of ethoxide can take place; for the present research, similar reactions could occur for the starting material as well as for 3 and 4, converting them into nonvolatile carboxylates. Scheme 1 shows a set of mechanistic steps that can account for the electrochemical behavior of 1.…”

Section: Controlled-potential Electrolysis Of Ethyl 2-bromo-3-(3 0 ; mentioning

confidence: 51%

Direct electrochemical reduction of a bromo-propargyloxy ester at vitreous carbon cathodes in dimethylformamide

Esteves

Goken

Klein

et al. 2003

Journal of Electroanalytical Chemistry

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Section: Controlled-potential Electrolysis Of Ethyl 2-bromo-3-(3 0 ; mentioning

confidence: 51%

Direct electrochemical reduction of a bromo-propargyloxy ester at vitreous carbon cathodes in dimethylformamide

Esteves

Goken

Klein

et al. 2003

Journal of Electroanalytical Chemistry

Self Cite

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“…[29,30] For cyclic voltammetry, we constructed a planar, circular working electrode with an area of 0.077 cm 2 by press-fitting a 3-mm-diameter glassy carbon rod (Grade GC-20, Tokai Electrode Manufacturing Company, Tokyo, Japan) into a Teflon shroud. Before each cyclic voltammogram was recorded, the electrode was cleaned with an aqueous suspension of 0.05-µm alumina on a Master-Tex (Buehler) polishing pad, after which the electrode was rinsed ultrasonically in a water bath.…”

Section: Mechanistic Aspects Of the Nickel(i) Salen Catalyzed Reductimentioning

confidence: 99%

Catalytic Reduction of Phenyl‐Conjugated Acetylenic Halides by Nickel(I) Salen: Cyclization versus Coupling

et al. 2007

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Cyclic voltammetry and controlled-potential electrolysis were employed to study the catalytic reduction of five phenyl-conjugated haloalkynes by nickel(I) salen electrogenerated at carbon cathodes in dimethylformamide containing tetramethylammonium tetrafluoroborate. Electrocatalytic reduction of 7-bromo-and 7-iodo-1-phenyl-1-heptyne affords the carbocyclic product, benzylidenecyclohexane, in up to 41 % yield, whereas under similar conditions reduction of 5-halo-1-phenyl-1-pentyne and 8-bromo-1-phenyl-1-octyne gives benzylidenecyclobutane and benzylidenecycloheptane, respectively, in very low yield (Յ1 %). Dimers, alkynes, and alkenynes are other products formed from the phenyl-

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“…Instrumentation for controlled-potential electrolyses is described in previous papers [9,10]. For cyclic voltammetry, we utilized a Faraday MP scanning potentiostat, model F02A (Obbligato Objectives, Inc.); experiments were performed with the aid of a companion computer program installed on a personal computer.…”

Section: Electrodes Cells Instrumentation and Proceduresmentioning

confidence: 99%

Electrochemical Reduction of 4,4′‐(2,2,2‐Trichloroethane‐1,1‐diyl)‐ bis(chlorobenzene) (DDT) and 4,4′‐(2,2‐Dichloroethane‐1,1‐diyl)‐ bis(chlorobenzene) (DDD) at Carbon Cathodes in Dimethylformamide

2006

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In dimethylformamide containing tetramethylammonium tetrafluoroborate, cyclic voltammograms for reduction of 4,4'-(2,2,2-trichloroethane-1,1-diyl)bis(chlorobenzene) (DDT) at a glassy carbon cathode exhibit five waves, whereas three waves are observed for the reduction of 4,4'-(2,2-dichloroethane-1,1-diyl)bis(chlorobenzene) (DDD). Bulk electrolyses of DDT and DDD afford 4,4'-(ethene-1,1-diyl)bis(chlorobenzene) (DDNU) as principal product (67 -94%), together with 4,4'-(2-chloroethene-1,1-diyl)bis(chlorobenzene) (DDMU), 1-chloro-4-styrylbenzene, and traces of both 1,1-diphenylethane and 4,4'-(ethane-1,1-diyl)bis(chlorobenzene) (DDO). For electrolyses of DDT and DDD, the coulometric n values are essentially 4 and 2, respectively. When DDT is reduced in the presence of a large excess of D 2 O, the resulting DDNU and DDMU are almost fully deuterated, indicating that reductive cleavage of the carbon -chlorine bonds of DDT is a two-electron process that involves carbanion intermediates. A mechanistic scheme is proposed to account for the formation of the various products.

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Catalytic reduction of ethyl chloroacetate by cobalt(I) salen electrogenerated at vitreous carbon cathodes

Cited by 61 publications

References 30 publications

Direct electrochemical reduction of a bromo-propargyloxy ester at vitreous carbon cathodes in dimethylformamide

Direct electrochemical reduction of a bromo-propargyloxy ester at vitreous carbon cathodes in dimethylformamide

Catalytic Reduction of Phenyl‐Conjugated Acetylenic Halides by Nickel(I) Salen: Cyclization versus Coupling

Electrochemical Reduction of 4,4′‐(2,2,2‐Trichloroethane‐1,1‐diyl)‐ bis(chlorobenzene) (DDT) and 4,4′‐(2,2‐Dichloroethane‐1,1‐diyl)‐ bis(chlorobenzene) (DDD) at Carbon Cathodes in Dimethylformamide

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