Issue 7, 1988
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Preparation of N,O-aminals as synthetic equivalents of H2C[double bond, length half m-dash]NAr and (H2C[double bond, length half m-dash]NHAr)+ ions: neutral- and acid-promoted transformations

José Barluenga,   Ana M. Bayón,   Pedro Campos,   Gregorio Asensio,   Elena Gonzalez-Nuñez  and  Yolanda Molina  

Abstract

A general method for the synthesis of N,O-aminals derived from primary aromatic amines is described. The reactivity of these compounds under neutral and acidic conditions has been studied and the title compounds can be envisaged as general purpose H2C[double bond, length half m-dash]NAr or (H2C[double bond, length half m-dash]NHAr)+ equivalents. N,O-Aminals have been converted into perhydrotriazines by moderate heating and into bis(4-aminoaryl)methane derivatives or N-benzylarylamines, respectively when heated in acidic media with pH control. Reduction of N,O-acetals with sodium cyanoborohydride has revealed that the C–O bond is broken exclusively in acidic media.

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Article information

DOI
https://doi.org/10.1039/P19880001631
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1988, 1631-1636

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Preparation of N,O-aminals as synthetic equivalents of H2C[double bond, length half m-dash]NAr and (H2C[double bond, length half m-dash]NHAr)+ ions: neutral- and acid-promoted transformations

J. Barluenga, A. M. Bayón, P. Campos, G. Asensio, E. Gonzalez-Nuñez and Y. Molina, J. Chem. Soc., Perkin Trans. 1, 1988, 1631 DOI: 10.1039/P19880001631

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