ORTHO METALATIONS - ADVANTAGE OF THE AMIDE FUNCTIONS

被引:92
作者
BEAK, P
BROWN, RA
机构
[1] Roger Adams Laboratory, University of Illinois
关键词
D O I
10.1021/jo01338a051
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of metalations of substituted N, N-diethylbenzamides by sec-butyllithium/tetramethylethylenediamine in tetrahydrofuran at -100°C shows the tertiary amide function to be superior to sulfonamide, oxazoline, methoxy, (dimethylamino)methyl, chloro, carboxyl, and methyl groups in directing lithiation to an adjacent position in intramolecular competitions. The Nmethyl amide is found to be somewhat better than the N, N-diethylamide group in the same competition. © 1979, American Chemical Society. All rights reserved.
引用
收藏
页码:4463 / 4464
页数:2
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