Abstract
A new approach for selective hydroxylation of non-activated cyclohexanes using dioxirane generated in situ in water through supramolecular control has been developed. Using β-CD and γ-CD as the supramolecular hosts, selective hydroxylation of cyclohexane substrates, including trans/cis-1,4-, 1,3-and 1,2-dimethylcyclohexanes and trans/cis-decahydronaphthalene, was achieved in up to 54% yield in water. Furthermore, site-selective C-H bond hydroxylation of (+)-menthol was achieved by obstructing the approach of dioxirane to the C-H bond with higher steric hindrance through inclusion complexation with β-CD and γ-CD in water.
Original language | English |
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Pages (from-to) | 30886-30893 |
Number of pages | 8 |
Journal | RSC Advances |
Volume | 7 |
Issue number | 49 |
DOIs | |
Publication status | Published - 1 Jan 2017 |
ASJC Scopus subject areas
- General Chemistry
- General Chemical Engineering