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The kinetics of reaction of copper with substituted benzyl bromides in dipolar aprotic solvents

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

Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
233 KB
Volume
37
Category
Article
ISSN
0538-8066

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✦ Synopsis

Abstract

The reaction of copper with benzyl bromides in dipolar aprotic solvents has been studied. There are no linear or other simple relations between ε, 1/ε, Y, P, n, and the rate of reaction. The activity of the solvent is determined by donor number (DN) in reaction under consideration. The kinetic and thermodynamic parameters of the reaction of copper with benzyl bromide in dimethyl sulfoxide (DMSO) have been clarified. Hammett plots of log (k/k°) vs. the substituent constant σ gave good correlations (ρ = 0.18, S~ρ~ = 0.02, r = 0.961 in dimethyl sulfoxide and ρ = 0.21, S~ρ~ = 0.02, r = 0.947 in dimethylacetamide (DMAA)). The structure of the organic group has little effect on the rate of reaction of benzyl bromide with copper. The Hammett ρ value also depends on DN. © 2005 Wiley Periodicals, Inc. Int J Chem Kinet 37: 496–501, 2005

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line 14: 1-phenoxy should read 2-phenoxy. Page 129, paragraph 3, line 10: the slope of the plot should read the slopes of the plots. Page 134, paragraph 2, lines 2-4: The reaction of pyrrolidine with 2c in acetonitrile is not base-catalyzed whereas that in DMSO is catalyzed should read The reaction