Issue 17, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Synthesis of imines, diimines and macrocyclic diimines as possible ligands, in aqueous solution

Alina Simion,a   Cristian Simion,a   Tadeshige Kanda,a   Satoko Nagashima,a   Yoshiharu Mitoma,a   Tomoko Yamada,a   Keisuke Mimuraa  and  Masashi Tashiro*b  

* Corresponding authors

a Tohwa Institute for Science, Tohwa University, 1-1-1 Chikushigaoka, Minami-ku, Fukuoka, Japan

b University of Southern California, Loker Hydrocarbon Research Institute, Department of Chemistry, Los Angeles, California, USA

Abstract

Although it is recognized that the presence of water is disadvantageous for imine synthesis, we demonstrate that such synthesis can be effective in completely aqueous media, without any catalyst and under mild conditions. Thus, aryl-aryl, aryl-alkyl, alkyl-aryl and alkyl-alkyl monoimines as well as a large variety of diimines are obtained by direct condensation of the corresponding carbonyl compounds and amines, in water. The same process is used to synthesize macrocyclic diimines starting from methylene, ethylene, trimethylene and tetramethylene glycol bis(2-formylphenyl ether) and ethylene-, trimethylene- and tetramethylene-diamine, some of these macrocycles being known for their chelating properties.

Graphical abstract: Synthesis of imines, diimines and macrocyclic diimines as possible ligands, in aqueous solution

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Article information

DOI
https://doi.org/10.1039/B102749M
Article type
Paper
Submitted
26 Mar 2001
Accepted
28 Jun 2001
First published
13 Aug 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 2071-2078

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Synthesis of imines, diimines and macrocyclic diimines as possible ligands, in aqueous solution

A. Simion, C. Simion, T. Kanda, S. Nagashima, Y. Mitoma, T. Yamada, K. Mimura and M. Tashiro, J. Chem. Soc., Perkin Trans. 1, 2001, 2071 DOI: 10.1039/B102749M

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