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Oxidative nitration of mononitroalkanes in a system sodium nitrite-polyhaloalkane

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Abstract

In reaction of nitroethane lithium salt with sodium nitrite in DMSO, DMF or HMPA involving polyhaloalkanes 1,1-dinitroethane formed in a high yield. The highest yield was obtained with bromo-and iododerivatives. The reaction fits to a kinetic equation of over all second order: the first with respect to the nitroethane anion, and the first in polyhaloalkane. The rate constants of the process are linearly dependent on the electron affinities of the perhaloalkanes molecules.

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Authors and Affiliations

  1. St. Petersburg State Technological Institute, St. Petersburg, 190013, Russia

    N. A. Petrova, M. B. Shcherbinin, A. G. Bazanov & I. V. Tselinskii

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  1. N. A. Petrova
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  2. M. B. Shcherbinin
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  3. A. G. Bazanov
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  4. I. V. Tselinskii
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Dedicated to Professor V.A. Ostrovskii on occasion of his sixtieth birthday

Original Russian Text © N.A. Petrova, M.B. Shcherbinin, A.G. Bazanov, I.V. Tselinskii, 2007, published in Zhurnal Organicheskoi Khimii, 2007, Vol. 43, No. 5, pp. 652–657.

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Petrova, N.A., Shcherbinin, M.B., Bazanov, A.G. et al. Oxidative nitration of mononitroalkanes in a system sodium nitrite-polyhaloalkane. Russ J Org Chem 43, 646–651 (2007). https://doi.org/10.1134/S1070428007050028

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  • DOI: https://doi.org/10.1134/S1070428007050028

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