Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
The first synthesis of the ribbon-like compounds 6-10 is described. The new building block diethyl 2,6-bis(bromomethyl)pyridine-3,5-dicarboxylate 1 was prepared and characterized. Single-crystal X-ray structure analyses indicate that these ribbon-like molecules arrange in a folded conformation, with the pyridine and benzene units being folded in a face-to-face manner, and the tosyl units of 8-10 pointing outwards. The “intramolecular self-assembly” (folding) of these molecular ribbons is primarily attributable to the energetically more favourable syn conformation of both the [3.3]metacyclophanes and the pyridinophanes.
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