Controlling photoreactions with restricted spaces and weak intermolecular forces: exquisite selectivity during oxidation of olefins by singlet oxygen

Natarajan, Arunkumar ; Kaanumalle, Lakshmi S. ; Jockusch, Steffen ; Gibb, Corinne L. D. ; Gibb, Bruce C. ; Turro, Nicholas J. ; Ramamurthy, V. (2007) Controlling photoreactions with restricted spaces and weak intermolecular forces: exquisite selectivity during oxidation of olefins by singlet oxygen Journal of American Chemical Society, 129 (14). pp. 4132-4133. ISSN 0002-7863

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Official URL: http://pubs.acs.org/doi/abs/10.1021/ja070086x

Related URL: http://dx.doi.org/10.1021/ja070086x

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.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:90045
Deposited On:04 May 2012 14:33
Last Modified:04 May 2012 14:33

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