359827-92-2Relevant academic research and scientific papers
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
Avdeenko,Konovalova,Il'chenko,Glinyanaya
, p. 56 - 65 (2007/10/03)
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 quin
Halogenation of N-substituted p-quinonimines and p-quinone oxime esters: I. Chlorination and bromination of 4-aroyloxyimino- and arylsulfonyloxyimino-2,5-cyclohexadienones
Avdeenko,Shishkina,Shishkin,Glinyanaya,Konovalova,Goncharova
, p. 683 - 691 (2007/10/03)
Chlorine and bromine addition to 4-aroyloxyimino- and 4-arylsulfonyloxymino-3-methyl-2,5-cyclohexadienones initially occurs at the C5=C6 double bond. The second chlorine molecule adds at both C2=C3 and C5=C6 double bonds. The chlorination of 2,5-dialkyl-substituted 4-aroyloxyimino- and 4-arylsulfonyloxymino-2,5-cyclohexadienones involves either of the C=C bonds in the quinoid ring.
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.
