Russian Journal of General Chemistry

, Volume 75, Issue 2, pp 285–289 | Cite as

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

  • P. B. Vorob’ev
  • D. Kh. Sembaev


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.


Oxide Methyl Vanadium Oxide Catalyst Cyano 
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Copyright information

© MAIK “Nauka/Interperiodica” 2005

Authors and Affiliations

  • P. B. Vorob’ev
    • 1
  • D. Kh. Sembaev
    • 1
  1. 1.Bekturov Institute of Chemical SciencesMinistry of Education and Science of KazakhstanAlmatyKazakhstan

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