Characterization and Singlet Oxygen Oxidation of 1-Alkyl Cyclohexenes Encapsulated Within a Water-Soluble Organic Capsule

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Abstract

Prompted by the selectivity observed during the oxidation of 1-methylcyclohexene included within a water-soluble capsule by singlet oxygen, we conducted oxidation of a number of 1-alkylcyclohexene derivatives. Of the three possible allylic hydrogens that could be abstracted by the attacking singlet oxygen, there was a preference for one of them but not to the extent that is observed with 1-methylcyclohexene. The observed high selectivity with 1-methylcyclohexene and moderate to low selectivity observed with longer n-alkyl substituted cyclohexenes is rationalized on the basis of the available free space around the three allylic hydrogens. A comparison of the behavior of eight 1-alkylcyclohexenes reveals that the behavior of confined reactant molecules cannot be extended based on a single model compound. The results presented demonstrate that the chemistry within supramolecular assemblies could be unique for each molecule just like in an enzyme.

Original languageEnglish (US)
Pages (from-to)655-666
Number of pages12
JournalChemPhotoChem
Volume2
Issue number7
DOIs
StatePublished - Jul 1 2018

Keywords

  • ene-reaction
  • organic capsules
  • photooxygenation
  • singlet oxygen
  • supramolecular photochemistry

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Analytical Chemistry

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