Russian Journal of Organic Chemistry

, Volume 42, Issue 1, pp 56–65 | Cite as

Halogenation of N-substituted p-quinone imines and p-quinone oxime esters: III. Regioselectivity in the halogenation of N-aroyl(arylsulfonyl)oxyimino-2,5-cyclohexadienones

  • A. P. Avdeenko
  • S. A. Konovalova
  • A. Ya. Il’chenko
  • N. M. Glinyanaya
Article

Abstract

Halogenation of 4-aroyl(arylsulfonyl)oxyimino-2,5-cyclohexadienones is not accompanied by change of the configuration at the nitrogen atom. p-Benzoquinone oxime ethers and esters take up halogens in a regioselective fashion at the syn-C-C bond of the quinoid ring. The main factor responsible for regioselective addition of halogens is configuration at the nitrogen atom, which determines the stability of intermediate halogenonium ion.

Keywords

Nitrogen Ether Ester Organic Chemistry Nitrogen Atom 

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Copyright information

© Pleiades Publishing, Inc. 2006

Authors and Affiliations

  • A. P. Avdeenko
    • 1
  • S. A. Konovalova
    • 1
  • A. Ya. Il’chenko
    • 2
  • N. M. Glinyanaya
    • 1
  1. 1.Donbass State Machine-Building AcademyKramatorsk-13Ukraine
  2. 2.Institute of Organic ChemistryNational Academy of Sciences of UkraineKiev 94Ukraine

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