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Halogenation of N-Substituted p-Quinonimines and p-Quinone Oxime Esters: I. Chlorination and Bromination of 4-Aroyloxyimino- and Arylsulfonyloxyimino-2,5-cyclohexadienones

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Abstract

Chlorine and bromine addition to 4-aroyloxyimino- and 4-arylsulfonyloxymino-3-methyl-2,5-cyclohexadienones initially occurs at the C5ÍC6 double bond. The second chlorine molecule adds at both C2ÍC and C5ÍC6 double bonds. The chlorination of 2,5-dialkyl-substituted 4-aroyloxyimino- and 4-arylsulfonyloxymino-2,5-cyclohexadienones involves either of the CÍC bonds in the quinoid ring.

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Authors and Affiliations

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

    A. P. Avdeenko, N. M. Glinyanaya, S. A. Konovalova & S. A. Goncharova

  2. Research Department of Alkali Metal Halide Crystals, Institut monokristallov Research and Technological Concern, National Academy of Sciences of Ukraine, Kharkiv, Ukraine

    S. V. Shishkina & O. V. Shishkin

Authors
  1. A. P. Avdeenko
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  2. S. V. Shishkina
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  3. O. V. Shishkin
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  4. N. M. Glinyanaya
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  5. S. A. Konovalova
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  6. S. A. Goncharova
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Avdeenko, A.P., Shishkina, S.V., Shishkin, O.V. et al. Halogenation of N-Substituted p-Quinonimines and p-Quinone Oxime Esters: I. Chlorination and Bromination of 4-Aroyloxyimino- and Arylsulfonyloxyimino-2,5-cyclohexadienones. Russian Journal of Organic Chemistry 38, 683–691 (2002). https://doi.org/10.1023/A:1019611105962

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