321946-34-3Relevant academic research and scientific papers
Halogenation of some alkyl-substituted 4-aroyloxyimino-and 4-arylsulfonyloxyimino-2,5-cyclohexadienones
Avdeenko,Zhukova,Konovalova
, p. 382 - 387 (2007/10/03)
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-C=C bond of the quinoid ring; simultaneous halogenation at both double bonds is not observed; halogen adds mainly across unsubstituted C=C bond; no halogenation occurs at the double bond already substituted by a halogen; bromination of the C=C bond with an alkyl substituent is more difficult than chlorination; the second halogen molecule adds only after regioselective dehydrohalogenation.
