Regioselectivity of the methanolysis of polychlorinated biphenyls

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 substituti...

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Bibliographic Details
Published in:Russian journal of general chemistry 2016-10, Vol.86 (10), p.2318-2324
Main Authors: Khaibulova, T. Sh, Boyarskaya, I. A., Polukeev, V. A., Boyarskii, V. P.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Chlorine
PCB
Polychlorinated biphenyls
Regioselectivity
Sodium
Substitutes
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Summary: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.
ISSN:1070-3632
1608-3350
DOI:10.1134/S1070363216100121