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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 30, Number 10
BKCSDE 30(10)
October 20, 2009 

Autoxidation of Cycloalkenes by the System “Molecular Oxygen-bis(acetylacetonato) Cobalt (II) Complex-butyraldehyde”
Zhao Fang, Rui ren Tang*, Rui rong Zhang, Ke long Huang
Epoxidation, Cycloalkenes, Acetylacetone cobalt (II), Molecular oxygen
Oxidation of cycloalkenes with O2 promoted by heterogeneous bis(acetylacetonato) cobalt (II) complex catalyst which can be recycled has been performed under mild conditions. It was found that β-ionone, cyclohexene, 1-methylcyclohexene, and α-ionone were efficiently oxidized with O2 in the presence of Co (II) complex and butyraldehyde at 55 oC. 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, α-pinene, and β-pinene gave allylic oxides as major products.
2208 - 2212
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