Direct and Indirect Electrochemical Reduction of Organic Halides in Aprotic Media
IR@CECRI: CSIR-Central Electrochemical Research Institute, Karaikudi
View Archive Info| Field | Value | |
| Title |
Direct and Indirect Electrochemical Reduction
of Organic Halides in Aprotic Media
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| Creator |
Vasudevan, D.
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| Subject |
Electroorganic
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| Description |
Cyclic voltammetric reduction of 17 different organic halides including alkyl, allyl, and benzyl
chlorides, bromides, and iodides in aprotic media (DMF, DMSO, and acetonitrile, AN), containing 0.1 M
Bu
4
NClO
4
, have been reported at glassy carbon (gc) and graphite as working electrodes. A single two-electron
irreversible and diffusion-limited reduction of the carbon–halogen bond is observed, the reduction potentials
ranging from –1.20 to –2.70 V (versus silver wire quasireference electrode) depending on the halide, the solvent,
and the electrode. Indirect reduction of these 17 halides, however, is effected at much lower potentials
(
−
0.79 to –0.92 V versus SCE) depending on the experimental conditions by
in situ
electrogenerated superoxide
ion ( ) by CPE. The products have been characterized by TLC, GC, CV, or chemical estimation. The diorganic
peroxide and the organic hydroperoxide were the major products. In case of tertiary alkyl halides, however,
alkenes predominated, due to basic nature of in these reactions. These studies indicate sufficient
strength of as a nucleophile or base depending on the experimental conditions.
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| Publisher |
Elektrokhimiya
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| Date |
2005
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| Type |
Article
PeerReviewed |
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| Format |
application/pdf
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| Identifier |
http://cecri.csircentral.net/176/1/092-2005.pdf
Vasudevan, D. (2005) Direct and Indirect Electrochemical Reduction of Organic Halides in Aprotic Media. Russian Journal of Electrochemistry, 41 (3). pp. 310-314. |
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| Relation |
http://cecri.csircentral.net/176/
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