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, Vaidhyanathan Ramamurthy

Research output: Contribution to journalArticle

137 Citations (Scopus)

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 languageEnglish
Pages (from-to)4132-4133
Number of pages2
JournalJournal of the American Chemical Society
Volume129
Issue number14
DOIs
StatePublished - Apr 11 2007

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Cycloparaffins
Singlet Oxygen
Photooxidation
Alkenes
Carboxylic Acids
Carboxylic acids
Olefins
Hydrogen
Oxidation
Oxygen
Water
cavitand

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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, Vaidhyanathan.

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

Research output: Contribution to journalArticle

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