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Kinetics and mechanism of benzyl chloride reaction with zinc in dimethylacetamide

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Abstract

Oxidative dissolution of zinc in the system of benzyl chloride-dimethylacetamide was investigated. The reaction stereochemistry as well as intermediates and reaction products formed were studied. The kinetic and thermodynamic parameters of the process were measured. The process was shown to follow the Langmuir-Hinshelwood mechanism with the formation of benzyl radicals and mono-solvated organozinc compound on the zinc surface. The components of mixture are adsorbed at various sites of the zinc surface, while recombination and the isomerization of the benzyl radicals occurs in solution.

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Authors and Affiliations

  1. Tula State University, pr. Lenina 92, Tula, 300600, Russia

    A. M. Egorov, S. A. Matyukhova & E. A. Dashkova

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  1. A. M. Egorov
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  2. S. A. Matyukhova
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  3. E. A. Dashkova
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Correspondence to S. A. Matyukhova.

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Original Russian Text © A.M. Egorov, S.A. Matyukhova, E.A. Dashkova, 2012, published in Zhurnal Obshchei Khimii, 2012, Vol. 82, No. 10, pp. 1675–1689.

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Egorov, A.M., Matyukhova, S.A. & Dashkova, E.A. Kinetics and mechanism of benzyl chloride reaction with zinc in dimethylacetamide. Russ J Gen Chem 82, 1686–1699 (2012). https://doi.org/10.1134/S107036321210009X

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  • DOI: https://doi.org/10.1134/S107036321210009X

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