An unexpected bispericyclic transition structure leading to 4+2 and 2+4 cycloadducts in the endo dimerization of cyclopentadiene

被引:163
作者
Caramella, P [1 ]
Quadrelli, P [1 ]
Toma, L [1 ]
机构
[1] Univ Pavia, Dipartimento Chim Organ, I-27100 Pavia, Italy
关键词
D O I
10.1021/ja016622h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The stereospecific endo dimerization of cyclopentadiene takes place through an asynchronous and symmetrical bispericyclic transition structure, which shows a merging of the 4+2 and 2+4 cycloaddition paths. The shape of the transition structure testifies to the presence of attractive Salem/Houk secondary orbital interactions assisting the endo approach. Copyright © 2002 American Chemical Society.
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页码:1130 / 1131
页数:2
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