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Kinetics of reaction of copper with substituted benzyl chlorides in dipolar aprotic solvents

✍ Scribed by Anatoly M. Egorov; Svetlana A. Matyukhova

Publisher
John Wiley and Sons
Year
2007
Tongue
English
Weight
299 KB
Volume
39
Category
Article
ISSN
0538-8066

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✦ Synopsis

Abstract

The reaction of copper with benzyl chlorides in dipolar aprotic solvents has been investigated. The kinetic and thermodynamic parameters of the reaction of copper with benzyl chloride in dimethyl sulfoxide, dimethylacetamide, and hexamethylphosphoramide have been obtained. Hammett plots of log (k/k°) versus the substituent constant σ gave good correlation. The structure of the organic group has little effect on the rate of reaction of benzyl chloride with copper. The kinetic and thermodynamic parameters were correlated with donor number of solvent (DN). The ratio k~RBr~/k~RCl~ and Hammett ρ values provide evidence in favor of the halogen atom transfer mechanism. © 2007 Wiley Periodicals, Inc. Int J Chem Kinet 39: 547–555, 2007

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