133368-88-4Relevant articles and documents
Direct Substitution of Aromatic Ethers by Lithium Amides. A New Aromatic Amination Reaction
Hoeve, Wolter ten,Kruse, Chris, G.,Luteyn, Jan M.,Thiecke, Janet R. G.,Wynberg, Hans
, p. 5101 - 5106 (1993)
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.