Halogenation of Some Alkyl-Substituted 4-Aroyloxyimino- and 4-Arylsulfonyloxyimino-2,5-cyclohexadienones |
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Authors: | A P Avdeenko S A Zhukova and S A Konovalova |
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Institution: | (1) Donbass State Machine-Building Academy, ul. Shkadinova 72, Kramatorsk, 343913, Ukraine |
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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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