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Mechanism and selectivity of radical alkylation of 3,4-Dichloro-2,5-dihydrofuran-2,5-dione

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Abstract

The mechanism of radical alkylation of 3,4-dichloro-2,5-dihydrofuran-2,5-dione with cyclohexane and 2,3-dimethylbutane follows an addition-elimination pattern with reversible formation of alkyl radicals. The proposed kinetic scheme takes into account the possibility for isomerization of primary 2,3-dimethylbutane radicals into tertiary and is consistent with the experimental data. The regioselectivity of the process is linearly related to the concentration of hydrogen chloride, so that the rate constant for the addition of primary 2,3-dimethylbutane radical to 3,4-dichloro-2,5-dihydrofuran-2,5-dione may be estimated. Effective procedures for the synthesis of 3-chloro-4-(2,3-dimethylbut-2-yl)-, 3-chloro-4-cyclohexyl-, and 3,4-dicyclohexyl-2,5-dihydrofuran-2,5-diones have been proposed.

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Authors and Affiliations

  1. St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia

    A. V. Trukhin, A. V. Messorosh, V. S. Karavan & E. V. Eliseenkov

Authors
  1. A. V. Trukhin
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  2. A. V. Messorosh
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  3. V. S. Karavan
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  4. E. V. Eliseenkov
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Additional information

Original Russian Text © A.V. Trukhin. A.V. Messorosh, V.S. Karavan, E.V. Eliseenkov, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 6, pp. 806–816.

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Trukhin, A.V., Messorosh, A.V., Karavan, V.S. et al. Mechanism and selectivity of radical alkylation of 3,4-Dichloro-2,5-dihydrofuran-2,5-dione. Russ J Org Chem 43, 801–811 (2007). https://doi.org/10.1134/S1070428007060024

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  • DOI: https://doi.org/10.1134/S1070428007060024

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