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Effect of the electronic structure of the radical anions of 4-substituted 1,2-and 1,3-dinitrobenzenes on the regioselectivity of reduction of the nitro groups

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Abstract

Theoretical and experimental regularities of the regioselectivity of the reduction of one of the two nitro groups in unsymmetrical dinitrobenzenes were studied. It was found that the regioselectivity of the formation of isomeric nitroanilines depends on the structure of the substrate and the nature of the reducing agent. The reduction regioselectivity model was verified, according to which radical anion protonation is the major reaction direction.

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Original Russian Text © V.Yu. Orlov, R.S. Begunov, N.Yu. Demidova, A.I. Rusakov, 2006, published in Zhurnal Obshchei Khimii, 2006, Vol. 76, No. 1, pp. 81–86.

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Orlov, V.Y., Begunov, R.S., Demidova, N.Y. et al. Effect of the electronic structure of the radical anions of 4-substituted 1,2-and 1,3-dinitrobenzenes on the regioselectivity of reduction of the nitro groups. Russ J Gen Chem 76, 76–81 (2006). https://doi.org/10.1134/S1070363206010154

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  • DOI: https://doi.org/10.1134/S1070363206010154

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