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Regioselectivity of the methanolysis of polychlorinated biphenyls

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Abstract

Regioselectivity of the methanolysis of lower polychlorinated biphenyls with sodium methoxide in a mixture of methanol and DMSO at 100–130°С was studied. It was found that 2,4,4'-tricholobiphenyl is much more reactive than 2,4-dichlorobiphenyl. This results in different mechanisms of substitution. 2,4-Dichlorobiphenyl reacts with sodium methoxide by the elimination–addition mechanism to form four monosubstitution products in comparable quantities. 2,4,4'-Trichlorobiphenyl reacts with the methodixe ion by the classical SNAr mechanism, with preferential substitution of the 2-chlorine atom.

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Authors and Affiliations

  1. St. Petersburg State University, Universitetskaya nab. 7–9, St. Petersburg, 199034, Russia

    T. Sh. Khaibulova, I. A. Boyarskaya & V. P. Boyarskii

  2. Institute of Experimental Medicine, St. Petersburg, Russia

    V. A. Polukeev

Authors
  1. T. Sh. Khaibulova
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  2. I. A. Boyarskaya
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  3. V. A. Polukeev
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  4. V. P. Boyarskii
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Correspondence to V. P. Boyarskii.

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Original Russian Text © T.Sh. Khaibulova, I.A. Boyarskaya, V.A. Polukeev, V.P. Boyarskii, 2016, published in Zhurnal Obshchei Khimii, 2016, Vol. 86, No. 10, pp. 1670–1677.

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Khaibulova, T.S., Boyarskaya, I.A., Polukeev, V.A. et al. Regioselectivity of the methanolysis of polychlorinated biphenyls. Russ J Gen Chem 86, 2318–2324 (2016). https://doi.org/10.1134/S1070363216100121

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  • DOI: https://doi.org/10.1134/S1070363216100121

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