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Halogenation of Some Alkyl-Substituted 4-Aroyloxyimino- and 4-Arylsulfonyloxyimino-2,5-cyclohexadienones

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Abstract

The chlorination and bromination of 2,3-dimethyl-, 3-methyl-6-isopropyl-, and 2,6-diisopropyl-4-aroyl(or arylsulfonyl)oxyimino-2,5-cyclohexadienones follow the proposed rules of halogenation of 4-aroyl(or arylsulfonyl)oxyimino-2,5-cyclohexadienones: the reaction occurs preferentially at the cis-CÍC bond of the quinoid ring; simultaneous halogenation at both double bonds is not observed; halogen adds mainly across unsubstituted CÍC bond; no halogenation occurs at the double bond already substituted by a halogen; bromination of the CÍC bond with an alkyl substituent is more difficult than chlorination; the second halogen molecule adds only after regioselective dehydrohalogenation.

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Authors and Affiliations

  1. Donbass State Machine-Building Academy, ul. Shkadinova 72, Kramatorsk, 343913, Ukraine

    A. P. Avdeenko, S. A. Zhukova & S. A. Konovalova

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  1. A. P. Avdeenko
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  2. S. A. Zhukova
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  3. S. A. Konovalova
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Avdeenko, A.P., Zhukova, S.A. & Konovalova, S.A. Halogenation of Some Alkyl-Substituted 4-Aroyloxyimino- and 4-Arylsulfonyloxyimino-2,5-cyclohexadienones. Russian Journal of Organic Chemistry 37, 382–387 (2001). https://doi.org/10.1023/A:1012403708255

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  • DOI: https://doi.org/10.1023/A:1012403708255

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