Cope reaction families:: To be or not to be a biradical

被引：53

作者：

Navarro-Vázquez, A

Prall, M

Schreiner, PR

机构：

[1] Univ Giessen, Inst Organ Chem, D-35392 Giessen, Germany

[2] Univ Georgia, Dept Chem, Athens, GA 30602 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 17期

关键词：

D O I：

10.1021/ol0488340

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cyclization reactions of polyunsaturated systems such as enediynes, enyne-allenes, as well as many others, can be structurally related to the Cope reaction and grouped into two branches: 6pi (e.g., Cope, allenyl-Cope) and [2sigma + 4pi] systems (e.g., Bergman, Myers-Saito). After extensive computional (BCCD(T)/cc-pVDZ/UBLYP/6-31G*) examination of a large set of Cope-related reactions, we derive the following simple rule: biradical intermediates are involved along the reaction path if they are stabilized by allylic resonance or aromaticity.

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页码：2981 / 2984

页数：4

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