DIRECTED LITHIATIONS - THE EFFECT OF VARYING DIRECTING GROUP ORIENTATION ON COMPETITIVE EFFICIENCIES FOR A SERIES OF TERTIARY AMIDE, SECONDARY AMIDE, AND ALKOXIDE DIRECTED ORTHO LITHIATIONS

被引：88

作者：

BEAK, P

KERRICK, ST

GALLAGHER, DJ

机构：

[1] Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1993年 / 115卷 / 23期

关键词：

D O I：

10.1021/ja00076a022

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Significant differences for competitive efficiencies in directed ortho lithiations for single functional groups in three series, the secondary benzamides 1-4, the tertiary benzamides 5-11, and the benzylic alcohols 12-17, are reported. For both amide series the efficiencies increase as the oxygen and ortho hydrogen in the substrate are more coplanar with the aromatic ring; however, for the alcohol series the opposite order is observed. Rationalizations are offered for these observations.

引用

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页码：10628 / 10636

页数：9

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