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：5
|
作者：
Avdeenko, AP
Konovalova, SA
Il'chenko, AY
Glinyanaya, NM
机构：
[1] Donbass State Machine Bldg Acad, UA-84313 Kramatorsk 13, Ukraine
[2] Natl Acad Sci Ukraine, Inst Organ Chem, Kiev 94, Ukraine
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 42卷 / 01期
关键词：
Nitrogen; Ether; Ester; Organic Chemistry; Nitrogen Atom;
D O I：
10.1134/S1070428006010106
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
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.
引用
收藏
页码：56 / 65
页数：10
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
    A. P. Avdeenko
    S. A. Konovalova
    A. Ya. Il’chenko
    N. M. Glinyanaya
    [J]. Russian Journal of Organic Chemistry, 2006, 42 : 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
    A. P. Avdeenko
    N. M. Glinyanaya
    S. A. Konovalova
    S. A. Goncharova
    [J]. Russian Journal of Organic Chemistry, 2002, 38 : 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
    Avdeenko, AP
    Glinyanaya, NM
    Konovalova, SA
    Goncharova, SA
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 38 (05) : 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
    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
  • [9] 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
  • [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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