Rings with A Twist

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Science  27 Jun 2003:
Vol. 300, Issue 5628, pp. 2007
DOI: 10.1126/science.300.5628.2007a

The formation of large macrocyclic rings during solution synthesis is often hindered by the entropy costs of closing the ring. Jiang and Lin report a “one-pot” synthesis that creates large chiral rings with three to eight units by catalytically coupling a flexible organic group bearing two ethyne linkages with trans-Pt(PEt3)2Cl2 (where Et is ethyl). The mix of products can be separated by column chromatography into the various size fractions as well as into their right- and left-handed components. The chiral fractions exhibit strong circular dichroism bands that arise from the arrangement of the PEt3 groups. Such chiral cavities may prove useful as artificial receptors in host-guest chemistry.—PDS

J. Am. Chem. Soc. 10.1021/ja034402t (2003).

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