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 |
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| Authors: | A. P. Avdeenko S. A. Konovalova A. Ya. Il’chenko N. M. Glinyanaya |
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| Affiliation: | (1) Donbass State Machine-Building Academy, ul. Shkadinova 72, Kramatorsk-13, 84313, Ukraine;(2) Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev 94, Ukraine |
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| 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. |
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