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

被引：12

作者：

Avdeenko, AP ^{[1
]}

Konovalova, SA ^{[1
]}

机构：

[1] Donbass State Machine Bldg Acad, UA-84313 Kramatorsk, Ukraine

来源：

RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 42卷 / 03期

关键词：

D O I：

10.1134/S1070428006030031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of halogens to N-arylsulfonyl-1,4-benzoquinone imines, which exist in a solution as Z and E isomers, is controlled by the steric factor. Z-E Isomerization strongly affects the stability of cyclohexene structures formed by halogenation of 1,4-benzoquinone imines. The halogenation of N-arylsulfonyl-1,4-benzoquinone imines was found to be accompanied by prototropic rearrangement.

引用

页码：349 / 364

页数：16

共 41 条

[21] 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
Russian Journal of Organic Chemistry, 2008, 44 : 542 - 552
[22] Halogenation of N-substituted para-quinone monoimine and para-quinone monooxime esters:: VI.: Regular trends in chlorination and bromination of N-arylsulfonyl-1,4-benzoquinone monoimines alkyl-substituted in the quinoid ring
Avdeenko, A. P.
Konovalova, S. A.
Ludchenko, O. N.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 42 (05) : 683 - 688
[23] Halogenation of N-substituted para-quinone monoimine and para-quinone monooxime esters: VI. Regular trends in chlorination and bromination of N-arylsulfonyl-1,4-benzoquinone monoimines alkyl-substituted in the quinoid ring
A. P. Avdeenko
S. A. Konovalova
O. N. Ludchenko
Russian Journal of Organic Chemistry, 2006, 42 : 683 - 688
[24] 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.
Russian Journal of Organic Chemistry, 2002, 38 (5) : 683 - 691
[25] 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
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 38 (05) : 683 - 691
[26] Halogenation of N-substituted p-quinone monoimines and p-quinone monooxime esters: XI. Synthesis and halogenation of 4-[aryl(alkyl)aminocarbonyl-oxyimino]cyclohexa-2,5-dien-1-ones
Avdeenko, A. P.
Konovalova, S. A.
Sergeeva, A. G.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 46 (06) : 830 - 843
[27] Activated Sterically Strained C=N Bond in N-Substituted p-Quinone Mono- and Diimines: XVII. Cyclohexene Polyhalogen Structures Originating from N-(Arylsulfonyl)-p-quinone Imines
A. P. Avdeenko
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Russian Journal of Organic Chemistry, 2018, 54 : 671 - 686
[28] Activated Sterically Strained C=N Bond in N-Substituted p-Quinone Mono- and Diimines: XVII. Cyclohexene Polyhalogen Structures Originating from N-(Arylsulfonyl)-p-quinone Imines
Avdeenko, A. P.
Konovalova, S. A.
Shishkina, S. V.
Omel'chenko, I. V.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 54 (05) : 671 - 686
[29] Halogenation of N-substituted p-quinone monoimines and p-quinone monooxime esrers: XI. Synthesis and halogenation of 4-[aryl(alkyl)aminocarbonyl-oxyimino]cyclohexa-2,5-dien-1-ones
A. P. Avdeenko
S. A. Konovalova
A. G. Sergeeva
Russian Journal of Organic Chemistry, 2010, 46 : 830 - 843
[30] Activated sterically strained C=N bond in N-substituted p-quinone mono- and diimines: XIV. Reaction of some 3,5-dimethyl-1,4-benzoquinone monoimines with alcohols
A. P. Avdeenko
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V. M. Vasil’eva
G. V. Palamarchuk
V. N. Baumer
O. V. Shishkin
Russian Journal of Organic Chemistry, 2013, 49 : 49 - 59

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