Differences in rates of Diels-Alder reactions as experimental indicators of synchronous or asynchronous transition states

被引：11

作者：

Buckle, RN ^{[1
]}

Liu, PY ^{[1
]}

Roberts, EWD ^{[1
]}

Burnell, DJ ^{[1
]}

机构：

[1] Mem Univ Newfoundland, Dept Chem, St Johns, NF A1B 3X7, Canada

来源：

TETRAHEDRON | 1999年 / 55卷 / 38期

基金：

加拿大自然科学与工程研究理事会;

关键词：

Diels-Alder reactions; steric and strain effects;

D O I：

10.1016/S0040-4020(99)00667-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Assessment of the relative rates of the Diels-Alder reactions of the unsymmetrical diene 2-(trimethylsilyloxy)-1,3-cyclohexadiene (1) and its 6,6- and 5,5-dimethyl analogs 2 and 3 indicated that with symmetrical, ethylenic dienophiles (para-benzoquinone, maleic anhydride and N-phenylmaleimide) the Diels-Alder reaction is almost synchronous, but with tetracyanoethylene and with diethyl acetylenedicarboxylate the addition is sufficiently asynchronous as to lead to different rates of reaction with dimethyl-dienes 2 and 3. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：11455 / 11464

页数：10

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