Direct substitution of aromatic ethers by lithium amides. A new aromatic amination reaction

W ten Hoeve, CG Kruse, JM Luteyn…

Index: Hoeve, Wolter ten; Kruse, Chris, G.; Luteyn, Jan M.; Thiecke, Janet R. G.; Wynberg, Hans Journal of Organic Chemistry, 1993 , vol. 58, # 19 p. 5101 - 5106

Full Text: HTML

Citation Number: 50

Abstract

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 ...

Related Articles:

Enantioselective synthesis and enhanced circularly polarized luminescence of S-shaped double azahelicenes

[Zhang, Yu; Yang, Xinye; Yao, Qizheng; Ma, Dawei Organic Letters, 2012 , vol. 14, # 12 p. 3056 - 3059]

Chemical Constitution, Electrochemical, Photographic and Allergenic Properties of p-Amino-N-dialkylanilines1

[Bent et al. Journal of the American Chemical Society, 1951 , vol. 73, p. 3100,3101]

Chemical Constitution, Electrochemical, Photographic and Allergenic Properties of p-Amino-N-dialkylanilines1

[Bent et al. Journal of the American Chemical Society, 1951 , vol. 73, p. 3100,3101]

More Articles...