The Tie that Switches the Bond

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Science  08 Sep 2000:
Vol. 289, Issue 5485, pp. 1655
DOI: 10.1126/science.289.5485.1655b

Just as enzymes can bring reacting groups together, reversible supramolecular assembly can catalyze reactions in solution. Bassani et al. have used such an assembly to redirect the outcome of a photochemical reaction, in this case the dimerization of a molecule containing a double bond to form a cyclobutane ring. The cinnamic acid derivative 1 (where Me is methyl) can bind through hydrogen bonds to both sides of the scaffold 2 and increase the yield of photoproducts. In the absence of 2, the predominant product is the “head to head” isomer 4a (where X is CO2Me and Ar is aryl), but in the presence of 2 the yield of the “head to tail” isomer 4c increases substantially. — PDS

J. Am. Chem. Soc., in press.

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