COMPETING RADICAL TRANSLOCATION REACTIONS OF TERTIARY N-(2-BROMOBENZYL)-ACETAMIDES AND N-(8-BROMONAPHTHYL)-ACETAMIDES

被引:40
作者
DENENMARK, D [1 ]
WINKLER, T [1 ]
WALDNER, A [1 ]
DEMESMAEKER, A [1 ]
机构
[1] CIBA GEIGY AG,CENT RES LABS,CH-4002 BASEL,SWITZERLAND
关键词
D O I
10.1016/S0040-4039(00)92516-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The radical translocation reactions in N,N-disubstituted acetamides 10a, 14a-d and trifluoroacetamides 10b, 14e-f have been studied by deuteration experiments with n-Bu3SnD. The intramolecular hydrogen atom transfer from the N-alkyl side chain to the aryl radical takes place through competing 6-, 7-, 8-membered ring transition states.
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页码:3613 / 3616
页数:4
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