Direct Oxidation of Cyclopropanated Cyclooctanes as a Synthetic Approach to Polycyclic Cyclopropyl Ketones

Article abstract of DOI:10.1002/ejoc.201701671

A series of polycyclic hydrocarbons containing cyclopropane moieties 1,2-annelated or spiro-condensed with a cyclooctane ring were investigated under oxidative conditions. Four oxidizing systems (O₃ on SiO₂, a dioxirane derived from trifluoroacetone, CrO₃, and RuO₄, generated in situ), were tested to evaluate and compare their reactivity and usefulness. RuO₄ was found to be the best of them, considering its oxidative power together with the simple operating procedure. Conditions for the specific oxidation of polycyclic hydrocarbons were found. New cyclooctane derivatives containing cyclopropyl carbonyl moieties were obtained.