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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

被引：0
|
作者：
A. P. Avdeenko
S. A. Konovalova
A. Ya. Il’chenko
N. M. Glinyanaya
机构：
[1] Donbass State Machine-Building Academy,Institute of Organic Chemistry
[2] National Academy of Sciences of Ukraine,undefined
来源：
Russian Journal of Organic Chemistry | 2006年 / 42卷
关键词：
Nitrogen; Ether; Ester; Organic Chemistry; Nitrogen Atom;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
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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页码：56 / 65
页数：9
相关论文
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  • [1] 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, AP
    Konovalova, SA
    Il'chenko, AY
    Glinyanaya, NM
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 42 (01) : 56 - 65
  • [2] Halogenation of N-substituted p-quinonimines and p-quinone oxime esters:: II.: Chlorination and bromination of 4-aroyl(arylsulfonyl)oxyimino-2-methyl-2,5-cyclohexadienones
    Avdeenko, AP
    Glinyanaya, NM
    Konovalova, SA
    Goncharova, SA
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 38 (05) : 692 - 698
  • [3] Halogenation of N-Substituted p-Quinonimines and p-Quinone Oxime Esters: II. Chlorination and Bromination of 4-Aroyl(arylsulfonyl)oxyimino-2-methyl-2,5-cyclohexadienones
    A. P. Avdeenko
    N. M. Glinyanaya
    S. A. Konovalova
    S. A. Goncharova
    [J]. Russian Journal of Organic Chemistry, 2002, 38 : 692 - 698
  • [4] Halogenation of N-substituted p-quinone monoimines and p-quinone monooxime esters:: VII.: Halogenation of 4-aroyl(arylsulfonyl)imino- and 4-aroyl(arylsulfonyl)oxyimino-2,6-diisopropylcyclohexa-2,5-dien-1-ones
    Avdeenko, A. P.
    Pirozhenko, V. V.
    Shishkin, O. V.
    Shishkina, S. V.
    Konovalova, S. A.
    Ludchenko, O. N.
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 44 (04) : 542 - 552
  • [5] Halogenation of N-substituted p-quinone monoimines and p-quinone monooxime esters: VII. Halogenation of 4-aroyl(arylsulfonyl)imino- and 4-aroyl(arylsulfonyl)-oxyimino-2,6-diisopropylcyclohexa-2,5-dien-1-ones
    A. P. Avdeenko
    V. V. Pirozhenko
    O. V. Shishkin
    S. V. Shishkina
    S. A. Konovalova
    O. N. Ludchenko
    [J]. Russian Journal of Organic Chemistry, 2008, 44 : 542 - 552
  • [6] Halogenation of N-substituted p-quinone monoimines and p-quinone monooxime esters:: VIII.: Halogenation of N-aroyl(arylsulfonyl)-2,6-di-tert-butyl-1,4-benzoquinone monoimines and their reduced forms
    Avdeenko, A. P.
    Pirozhenko, V. V.
    Shishkin, O. V.
    Palamarchuk, G. V.
    Zubatyuk, R. I.
    Konovalova, S. A.
    Ludchenko, O. N.
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 44 (06) : 807 - 813
  • [7] Halogenation of n-substituted p-quinone monoimines and p-quinone monooxime esters: VIII. Halogenation of N-aroyl(arylsulfonyl)-2,6-di-tert-butyl-1,4-benzoquinone monoimines and their reduced forms
    A. P. Avdeenko
    V. V. Pirozhenko
    O. V. Shishkin
    G. V. Palamarchuk
    R. I. Zubatyuk
    S. A. Konovalova
    O. N. Ludchenko
    [J]. Russian Journal of Organic Chemistry, 2008, 44 : 807 - 813
  • [8] Halogenation of N-substituted p-quinonimines and p-quinone oxime esters:: I.: Chlorination and bromination of 4-aroyloxyimino- and arylsulfonyloxyimino-2,5-cyclohexadienones
    Shishkina, SV
    Shishkina, SV
    Shishkin, OV
    Glinyanaya, NM
    Konovalova, SA
    Goncharova, SA
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 38 (05) : 683 - 691
  • [9] Halogenation of N-substituted p-quinonimines and p-quinone oxime esters: I. Chlorination and bromination of 4-aroyloxyimino- and arylsulfonyloxyimino-2,5-cyclohexadienones
    Avdeenko A.P.
    Shishkina S.V.
    Shishkin O.V.
    Glinyanaya N.M.
    Konovalova S.A.
    Goncharova S.A.
    [J]. Russian Journal of Organic Chemistry, 2002, 38 (5) : 683 - 691
  • [10] Halogenation of N-substituted p-quinone imines and p-quinone oxime esters: IV. Chlorination and bromination of N-arylsulfonyl-2(3)-methyl(2-chloro)-1,4-benzoquinone monoimines
    A. P. Avdeenko
    S. A. Konovalova
    [J]. Russian Journal of Organic Chemistry, 2006, 42 : 349 - 364
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