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Mechanism of Formation of the Cyano Group from the Chloromethyl, Methoxymethyl, and Alkoxycarbonyl Substituents in the Aromatic Ring Under Conditions of Oxidative Ammonolysis

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Abstract

Upon gas-phase oxidative ammonolysis on vanadium oxide catalysts 4-nitro-, 2-halo, 2- and 4-hydroxy-, and 4-methoxy- and 4-phenoxytoluenes much less selectively convert into the corresponding substituted benzonitriles than their derivatives with the methyl group substituted by chloromethyl, methoxymethyl, or alkoxycarbonyl groups. This fact is explained in terms of different mechanisms of formation of the cyano group: The methyl group converts via deprotonation to form a carbanion, whereas the heteroatomic groups, via the energetically more favorable carbocation formation.

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Authors and Affiliations

  1. Bekturov Institute of Chemical Sciences, Ministry of Education and Science of Kazakhstan, Almaty, Kazakhstan

    P. B. Vorob’ev & D. Kh. Sembaev

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  1. P. B. Vorob’ev
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  2. D. Kh. Sembaev
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__________

Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 2, 2005, pp. 313–317.

Original Russian Text Copyright © 2005 by Vorob’ev, Sembaev.

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Vorob’ev, P.B., Sembaev, D.K. Mechanism of Formation of the Cyano Group from the Chloromethyl, Methoxymethyl, and Alkoxycarbonyl Substituents in the Aromatic Ring Under Conditions of Oxidative Ammonolysis. Russ J Gen Chem 75, 285–289 (2005). https://doi.org/10.1007/s11176-005-0214-1

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  • DOI: https://doi.org/10.1007/s11176-005-0214-1

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