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Issue 16, 1976
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Application of the macrocyclic polyether 18-crown-6 to the synthesis of N-alkyl- or - aryl-2-(p-nitrophenoxy)ethylamines

Anthony C. Knipe,  Narayan Sridhar  and  Anna Loughran 

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.

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Article type: Paper
DOI: 10.1039/C3976000630A
Citation: J. Chem. Soc., Chem. Commun., 1976,0, 630a-630a
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    Application of the macrocyclic polyether 18-crown-6 to the synthesis of N-alkyl- or - aryl-2-(p-nitrophenoxy)ethylamines

    A. C. Knipe, N. Sridhar and A. Loughran, J. Chem. Soc., Chem. Commun., 1976, 0, 630a
    DOI: 10.1039/C3976000630A

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