NUCLEOPHILIC CLEAVAGES OF ONE-ELECTRON SIGMA-BONDS ARE PREDICTED TO PROCEED WITH STEREOINVERSION

被引：50

作者：

SHAIK, SS ^{[1
]}

DINNOCENZO, JP ^{[1
]}

机构：

[1] UNIV ROCHESTER,DEPT CHEM,ROCHESTER,NY 14627

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 11期

关键词：

D O I：

10.1021/jo00298a004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

: The valence-bond curve crossing model is used to analyze the stereochemistry of nucleophilic displacements on one-electron σ bonds. The model predicts that the stereochemistry of cleavage of one-electron a bond by nucleophiles will be governed by the a* orbital of the one-electron bonds. As a result such nucleophilic cleavages are predicted to proceed with inversion of stereochemistry at the center of attack. This prediction is in accord with recent experimental findings. © 1990, American Chemical Society. All rights reserved.

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页码：3434 / 3436

页数：3

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