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Kinetics and mechanism of the reaction of benzyl bromide with copper in hexamethylphosphoramide

✍ Scribed by Anatoly M. Egorov; Svetlana A. Matyukhova; Alexander V. Anisimov

Publisher: John Wiley and Sons
Year: 2005
Tongue: English
Weight: 163 KB
Volume: 37
Category: Article
ISSN: 0538-8066
DOI: 10.1002/kin.20065

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✦ Synopsis

Abstract

The reaction of copper with benzyl bromides in hexamethylphosphoramide has been studied. The kinetic and thermodynamic parameters of the reaction have been obtained. Hammett plots of log (k/k^o^) vs the substituent constant σ gave good correlations (ρ = 0.15, S~ρ~ = 0.02, r = 0.954). The structure of the organic group has little effect on the rate of reaction of benzyl bromide with copper. In the absence of atmospheric oxygen, the oxidative dissolution of copper occurred by the mechanism of single‐electron transfer with the formation of 1,2‐diphenylethane and copper(I) complexes. The stereochemistry and intermediates compound was also investigated.

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