Application of the macrocyclic polyether 18-crown-6 to the synthesis of N-alkyl- or - aryl-2-(p-nitrophenoxy)ethylamines

Abstract

N-Alkyl- or N-aryl-2-(p-nitrophenoxy)ethylamines (II) have been synthesized by desulphonative Smiles′ rearrangement of N-alkyl- or N-aryl-N-(2-hydroxyethyl)-p-nitrobenzenesulphonamides (I) which is promoted by reaction with 18-crown-6-complexed potassium hydroxide in methylene chloride; the subsequent Smiles′ rearrangement of (II) to the corresponding N-alkyl- or N-aryl-2-(p-nitroanilino)ethanols (III) is thus effectively prevented.