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School of Engineering and Science, Organic and Analytical Chemistry Laboratory, Jacobs University Bremen, Campus ring 1, P. O. Box. 750 561, 28725 Bremen, Germany
; Fax: (+)49 421 200 3229
Org. Biomol. Chem., 2012,10, 4381-4389
22 Jan 2012,
03 Apr 2012
First published online
03 Apr 2012
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.
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Organic & Biomolecular Chemistry
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