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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