TANDEM ENYNE ALLENE-RADICAL CYCLIZATION VIA [3,3]-SIGMATROPIC REARRANGEMENTS

被引:30
|
作者
GRISSOM, JW
HUANG, DH
机构
[1] Department of Chemistry, University of Utah, Salt Lake City
来源
JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 18期
关键词
D O I
10.1021/jo00097a002
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enediynes 1, 7, 12, and 16 undergo a tandem [3,3] sigmatropic shift-enyne allene cyclization. Enediynes 7 and 16 are especially interesting because after undergoing a [3,3] sigmatropic shift and enyne allene cyclization, the resultant biradical undergoes a 5-exo radical cyclization. These reactions can be effected by either heating at 150 degrees C or by treatment with silver salts followed by heating at 75 degrees C.
引用
收藏
页码:5114 / 5116
页数:3
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