Autoxidation of Cycloalkenes by the System “Molecular Oxygen-bis(acetylacetonato) Cobalt (II) Complex-butyraldehyde”

Oxidation of cycloalkenes with $O_2$ promoted by heterogeneous bis(acetylacetonato) cobalt (II) complex catalyst which can be recycled has been performed under mild conditions. It was found that $\beta$-ionone, cyclohexene, 1-methylcyclohexene, and $\alpha$-ionone were efficiently oxidized with $O_2$ in the presence of Co (II) complex and butyraldehyde at $55\;{^{\circ}C}$. A simple treatment of the resulting products led to epoxides as predominant products and a small amounts of allylic oxides, the chemoselectivity for the former being 82.1 - 90.8% with a 70.6 - 98.6% substrate conversion. On the other hand, oxidation of 1-phenylcyclohexene, 1-cyclohex-1-enylethan-1-one, $\alpha$-pinene, and $\beta$-pinene gave allylic oxides as major products.