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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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Publication details

The article was received on 11 Dec 2002, accepted on 29 Jan 2003 and first published on 12 Mar 2003


Article type: Paper
DOI: 10.1039/B212102F
Citation: Org. Biomol. Chem., 2003,1, 1157-1170
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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

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

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