THE CIEPLAK EFFECT - HYPERCONJUGATIVE INTERACTIONS IN DIELS-ALDER REACTIONS

被引：56
作者：
COXON, JM
MCDONALD, DQ
机构：
[1] Department of Chemistry, University of Canterbury, Christchurch
来源：
TETRAHEDRON LETTERS | 1992年 / 33卷 / 05期
关键词：
D O I：
10.1016/S0040-4039(00)92334-7
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Molecular orbital calculations of the transition states for the reactions of the dienes la-e with ethylene using the AM1 Hamiltonian show the diene C-X bond length for anti addition of the dienophile is longer than the comparable bond length when the X-substituent is syn to the approaching dienophile. The bond lengthening is consistent with hyperconjugative stabilization involving the donation of electron density from the sigma-bond of the anti substituent to the forming sigma*-orbital.
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页码：651 / 654
页数：4
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