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

Arunkumar Natarajan; Lakshmi S. Kaanumalle; Steffen Jockusch; Corinne L.D. Gibb; Bruce C. Gibb; Nicholas J. Turro; V. Ramamurthy

doi:10.1021/ja070086x

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

Arunkumar Natarajan, Lakshmi S. Kaanumalle, Steffen Jockusch, Corinne L.D. Gibb, Bruce C. Gibb, Nicholas J. Turro, V. Ramamurthy

Chemistry

Research output: Contribution to journal › Article

138 Scopus citations

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.

Original language	English (US)
Pages (from-to)	4132-4133
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	129
Issue number	14
DOIs	https://doi.org/10.1021/ja070086x
State	Published - Apr 11 2007

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ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

Cite this

Natarajan, A., Kaanumalle, L. S., Jockusch, S., Gibb, C. L. D., Gibb, B. C., Turro, N. J., & Ramamurthy, V. (2007). Controlling photoreactions with restricted spaces and weak intermolecular forces: Exquisite selectivity during oxidation of olefins by singlet oxygen. Journal of the American Chemical Society, 129(14), 4132-4133. https://doi.org/10.1021/ja070086x

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.

In: Journal of the American Chemical Society, Vol. 129, No. 14, 11.04.2007, p. 4132-4133.

Research output: Contribution to journal › Article

Natarajan, Arunkumar ; Kaanumalle, Lakshmi S. ; Jockusch, Steffen ; Gibb, Corinne L.D. ; Gibb, Bruce C. ; Turro, Nicholas J. ; Ramamurthy, V. / Controlling photoreactions with restricted spaces and weak intermolecular forces : Exquisite selectivity during oxidation of olefins by singlet oxygen. In: Journal of the American Chemical Society. 2007 ; Vol. 129, No. 14. pp. 4132-4133.

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10.1021/ja070086x