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Issue 22, 2012
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Synthesis of novel enantiomerically pure tetra-carbohydrazide cyclophane macrocycles

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Abstract

A total of twelve novel enantiomerically pure tetra-carbohydrazide cyclophane macrocycles have been synthesised in quantitative yields by reacting chiral (4R,5R)- and (4S,5S)-1,3-dioxolane-4,5-dicarbohydrazides with aromatic bis-aldehydes in a [2 + 2]-cyclocondensation reaction. The compounds show a dynamic behaviour in solution, which has been rationalized in terms of an unprecedented conformational interconversion between two conformers one stabilised by intramolecular hydrogen bonding and π–π stacking interactions.

Graphical abstract: Synthesis of novel enantiomerically pure tetra-carbohydrazide cyclophane macrocycles

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Publication details

The article was received on 22 Jan 2012, accepted on 03 Apr 2012 and first published on 03 Apr 2012


Article type: Paper
DOI: 10.1039/C2OB25171J
Citation: Org. Biomol. Chem., 2012,10, 4381-4389
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    Synthesis of novel enantiomerically pure tetra-carbohydrazide cyclophane macrocycles

    H. F. Nour, N. Hourani and N. Kuhnert, Org. Biomol. Chem., 2012, 10, 4381
    DOI: 10.1039/C2OB25171J

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