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Halogenation of N-substituted p-quinone monoimines and p-quinone monooxime esters: VII. Halogenation of 4-aroyl(arylsulfonyl)imino- and 4-aroyl(arylsulfonyl)-oxyimino-2,6-diisopropylcyclohexa-2,5-dien-1-ones

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Abstract

Halogenation of 4-aroyl(arylsulfonyl)imino-2,6-diisopropylcyclohexa-2,5-dien-1-ones gave 4-aroyl-(arylsulfonyl)imino-3-halo-2,6-diisopropylcyclohexa-2,5-dien-1-ones and 4-aroyl(arylsulfonyl)imino-3,5,6-trihalo-2,6-diisopropylcyclohex-2-en-1-ones. The latter were formed as mixtures of two stereoisomers, and the isopropyl group on the sp 3-hybridized carbon atom in one stereoisomer occupies axial position, which is untypical of such compounds. Halogenation of 4-aroyl(arylsulfonyl)oxyimino-2,6-diisopropylcyclohexa-2,5-dien-1-ones leads to the formation of the corresponding addition products with traditional trans-diaxial arrangement of the halogen atoms.

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Authors and Affiliations

  1. Donbass State Machine-Building Academy, ul. Shkadinova 72, Kramatorsk, 84313, Ukraine

    A. P. Avdeenko, S. A. Konovalova & O. N. Ludchenko

  2. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev, Ukraine

    V. V. Pirozhenko

  3. Institute of Single Crystals, National Academy of Sciences of Ukraine, Khar’kov, Ukraine

    O. V. Shishkin & S. V. Shishkina

Authors
  1. A. P. Avdeenko
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  2. V. V. Pirozhenko
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  3. O. V. Shishkin
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  4. S. V. Shishkina
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  5. S. A. Konovalova
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  6. O. N. Ludchenko
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Correspondence to A. P. Avdeenko.

Additional information

Original Russian Text © A.P. Avdeenko, V.V. Pirozhenko, O.V. Shishkin, S.V. Shishkina, S.A. Konovalova, O.N. Ludchenko, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 4, pp. 547–557.

For communication VI, see [1].

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Avdeenko, A.P., Pirozhenko, V.V., Shishkin, O.V. et al. Halogenation of N-substituted p-quinone monoimines and p-quinone monooxime esters: VII. Halogenation of 4-aroyl(arylsulfonyl)imino- and 4-aroyl(arylsulfonyl)-oxyimino-2,6-diisopropylcyclohexa-2,5-dien-1-ones. Russ J Org Chem 44, 542–552 (2008). https://doi.org/10.1134/S1070428008040131

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  • DOI: https://doi.org/10.1134/S1070428008040131

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