The Diels-Alder reactions of para-benzoquinone nitrogen-derivatives: an experimental and theoretical study

被引：15
|
作者：
Uliana, Marciana P. [1 ]
Servilha, Bruno M. [1 ]
Alexopoulos, Olga [1 ]
de Oliveira, Kleber T. [1 ]
Tormena, Claudio F. [2 ]
Ferreira, Marco A. B. [1 ]
Brocksom, Timothy J. [1 ]
机构：
[1] Univ Fed Sao Carlos, Dept Quim, BR-13560905 Sao Carlos, SP, Brazil
[2] Univ Estadual Campinas, Inst Quim, Dept Quim Organ, BR-13083970 Campinas, SP, Brazil
来源：
TETRAHEDRON | 2014年 / 70卷 / 39期
基金：
瑞典研究理事会; 巴西圣保罗研究基金会;
关键词：
Diels-Alder reaction; para-Benzoquinone nitrogen-derivatives; Theoretical study; ABSOLUTE-CONFIGURATION; DENSITY FUNCTIONALS; HYDROGEN-PEROXIDE; OXIDATION; QUINONES; CHEMISTRY; PHENOLS; CHLORINATION; HALOGENATION; BROMINATION;
D O I：
10.1016/j.tet.2014.07.088
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An experimental and theoretical study of the comparative reactivity and selectivity of the Diels-Alder reactions of para-benzoquinones and three nitrogen derivatives have been performed. The mono-oximes derivatives do not react under the tested reaction conditions, whereas the tosylated mono-oximes react slowly. However, the mono N-tosyl imines show excellent reactivity, and superior to the parent para-benzoquinones. DFT calculations support these experimental results. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6963 / 6973
页数：11
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