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Issue 7, 2003
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The synthesis of trianglimines: on the scope and limitations of the [3 + 3] cyclocondensation reaction between (1R,2R)-diaminocyclohexane and aromatic dicarboxaldehydes

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Abstract

The synthesis of aromatic dicarboxaldehydes, using dilithiation methodology is described along with their reactivity, in the [3 + 3] cyclocondensation reaction, with (1R,2R)-diaminocyclohexane to give trianglimine macrocycles. The scope and limitations of the cyclocondensation reaction are studied and some comments on the properties of the novel macrocycles are made such as their conformation in solution and temperature dependent dynamic NMR behaviour.

Graphical abstract: The synthesis of trianglimines: on the scope and limitations of the [3 + 3] cyclocondensation reaction between (1R,2R)-diaminocyclohexane and aromatic dicarboxaldehydes

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Article information


Submitted
11 Dec 2002
Accepted
29 Jan 2003
First published
12 Mar 2003

Org. Biomol. Chem., 2003,1, 1157-1170
Article type
Paper

The synthesis of trianglimines: on the scope and limitations of the [3 + 3] cyclocondensation reaction between (1R,2R)-diaminocyclohexane and aromatic dicarboxaldehydes

N. Kuhnert, G. M. Rossignolo and A. Lopez-Periago, Org. Biomol. Chem., 2003, 1, 1157
DOI: 10.1039/B212102F

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