Controlling Photoreactions with Restricted Spaces and Weak Intermolecular Forces: Exquisite Selectivity during Oxidation of Olefins by Singlet Oxygen
Journal of the American Chemical Society2007Vol. 129(14), pp. 4132–4133
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Arunkumar Natarajan, Lakshmi S. Kaanumalle, Steffen Jockusch, Corinne L. D. Gibb, Bruce C. Gibb, Nicholas J. Turro, V. Ramamurthy
Abstract
Highly regioselective photooxidation of methyl cycloalkenes has been performed in an aqueous medium by selectively blocking two of the three allylic hydrogens through supramolecular steric effect. Hydrophobic, steric, and weak intermolecular C−H−π interactions are suggested to be responsible for the specific orientation of the olefin within a water-soluble, deep-cavity cavitand with eight carboxylic acid groups.
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