DIRECT SUBSTITUTION OF AROMATIC ETHERS BY LITHIUM AMIDES - A NEW AROMATIC AMINATION REACTION

被引:51
作者
TENHOEVE, W
KRUSE, CG
LUTEYN, JM
THIECKE, JRG
WYNBERG, H
机构
[1] SYNCOM BV,NYENBORGH 4,9747 AG GRONINGEN,NETHERLANDS
[2] SOLVAY DUPHAR RES LABS,1380 DA WEESP,NETHERLANDS
关键词
D O I
10.1021/jo00071a019
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of lithiated dialkylamines with methoxy aromatics in refluxing THF leads to products resulting from a direct ipso-substitution. Especially with lithiated secondary amines high conversions and selectivities are achieved. Sulfonyl-substituted aromatics react equally well, but halogenated aromatics give rise to side-products arising from a competing pathway via aryne intermediates. The scope and mechanistic implications of this novel nucleophilic amination reaction are described.
引用
收藏
页码:5101 / 5106
页数:6
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