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

Research output: Contribution to journalArticle

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

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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