Regiochemistry in aryl radical cyclisations (5-exo versus 6-endo) of N-vinylic 2-iodobenzamides

被引：46
|
作者：
Ishibashi, H
Ohata, K
Niihara, M
Sato, T
Ikeda, M
机构：
[1] Kanazawa Univ, Fac Pharmaceut Sci, Kanazawa, Ishikawa 9200934, Japan
[2] Kyoto Pharmaceut Univ, Kyoto 6078414, Japan
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 04期
关键词：
D O I：
10.1039/a908678a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Bu3SnH-mediated aryl radical cyclisations of a range of N-vinylic 2-iodobenzamides 10 were examined. The enamides 10a-d gave exclusively the 5-exo cyclisation products 11a-d, whereas the enamides 10e,f having a phenyl substituent on the vinylic carbon atom alpha to the nitrogen atom gave predominantly the 6-endo cyclisation products 14 and 18, respectively. The experiments on the effect of concentration of Bu3SnH or temperature on the products distribution showed that the formation of the 6-endo cyclisation products 14 and 18 was a result of a 5-exo cyclisation of the aryl radicals formed from 10e,f followed by neophyl rearrangement of the intermediate radicals.
引用
收藏
页码：547 / 553
页数：7
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