STEREOCHEMISTRY OF DIELS-ALDER REACTION . SYN-ANTI ISOMERISM

被引:105
作者
WILLIAMS.KL
HSU, YFL
LACKO, R
YOUN, CH
机构
[1] Department of Chemistry, Mount Holyoke College, South Hadley
关键词
D O I
10.1021/ja01050a035
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Electronic and steric factors governing syn-anti isomerism in the Diels-Alder reaction have been investigated employing 1,2,3,4,5-pentachlorocyclopentadiene as the plane asymmetric dienophile. The predominance of anti-7-chloro isomers in many cases has been ascribed to forces arising from dipole-dipole, dipole-induced dipole, and London-dispersion interactions, the predominance of endo over exo isomers to secondary orbital interactions and the lack of anti-exo isomers to steric hinderance in the transition state. © 1969, American Chemical Society. All rights reserved.
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页码:6129 / +
页数:1
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