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Characterization and Singlet Oxygen Oxidation of 1‐Alkyl Cyclohexenes Encapsulated Within a Water‐Soluble Organic Capsule
Author(s) -
Gupta Shipra,
Ramamurthy Vaidhyanathan
Publication year - 2018
Publication title -
chemphotochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.13
H-Index - 18
ISSN - 2367-0932
DOI - 10.1002/cptc.201800043
Subject(s) - allylic rearrangement , singlet oxygen , selectivity , alkyl , chemistry , oxygen , molecule , photochemistry , singlet state , supramolecular chemistry , organic chemistry , catalysis , excited state , physics , nuclear physics
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.