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.
- organic capsules
- singlet oxygen
- supramolecular photochemistry
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Analytical Chemistry