THE REACTIONS OF AN ORTHO-QUINONE MONOIMIDE WITH SOME PHENOLS

被引：5

作者：

HEINE, HW ^{[1
]}

CIACCIO, JA ^{[1
]}

CARSON, KG ^{[1
]}

TAYLOR, CM ^{[1
]}

WILLIAMS, EA ^{[1
]}

机构：

[1] GE CO,CORP RES & DEV,SCHENECTADY,NY 12309

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 13期

关键词：

D O I：

10.1021/jo00300a018

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The o-quinone monoimide N-(2,4-dichloro-6-oxo-2,4-cyclohexadien-l-ylidene)-4-nitrobenzamide (1) reacts with 2.6-dimethoxy-, 2,6-dimethyl-, and 2,6-dichlorophenols (2a-c) to form N-(2,4-dichloro-6-hydroxyphenyl)-N-(3,5-dimethoxy-, 3,5-dimethyl-, 3,5-dichloro-4-hydroxy)-4-nitrobenzamides (3a-c), respectively. Oxidation of 3a by 1 and 3b by DDQ lead to N-aryl-p-iminoquinones 4a,b. Oxidative dimerizations by either C-C or C-O coupling occur when 1 is admixed with the sterically hindered 2,6-di-tert-butyl-, 2,4-di-£er£-butyl-, 4-bromo-2.6-di-£er£-butyl-, and 2,4,6-tri-£ert-butylphenols. © 1990, American Chemical Society. All rights reserved.

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页码：4039 / 4043

页数：5

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