New 2+2, 3+3 and 4+4 macrocycles derived from 1,2-diaminocyclohexane and 2,6-diformylpyridine
- 15 July 2005
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 3 (17) , 3161-3166
- https://doi.org/10.1039/b505909g
Abstract
Two new Schiff base macrocycles – a 4+4 condensation product and a meso-type 2+2 condensation product – were obtained in a reaction of trans-1,2-diaminocyclohexane and 2,6-diformylpyridine. Reduction of these compounds led to the corresponding 4+4 and 2+2 macrocyclic amines. The macrocycles were characterised by NMR spectroscopy and electrospray mass spectrometry. The symmetry and stereochemistry of these macrocycles, as well as of new 3+3 and 4+4 diastereomers identified in solution, has been established. X-Ray structures of the 2+2 and 4+4 Schiff base macrocycles confirm the configurations determined on the basis of spectroscopic investigations. The crystal structures reveal that the centres of the square-shaped 4+4 macrocycles form channels as a result of columnar stacking.Keywords
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