[CH2:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH:7]N1C(=O)N(O)C(=O)N(O)[C:9]1=[O:18].[O:19]=O.[C:21]([OH:24])(=[O:23])[CH3:22]>C([O-])(=O)C.[Co+2].C([O-])(=O)C.C([O-])(=O)C.[Mn+2].C([O-])(=O)C>[C:1]1(=[O:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:9]([OH:18])(=[O:19])[CH2:2][CH2:1][CH2:6][CH2:22][C:21]([OH:24])=[O:23].[C:9]([OH:18])(=[O:19])[CH2:6][CH2:1][CH2:22][C:21]([OH:24])=[O:23]A mixture of 1.00 g of cyclohexane, 0.063 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (3% by mole relative to cyclohexane), 29.0 g of acetic acid, 0.015 g of cobalt(II) acetate.4H2O and 0.015 g of manganese(II) acetate.4H2O was stirred at 100° C. in an atmosphere of oxygene gas (1 atm=0.1 MPa) for 8 hours. The resulting product in the reaction mixture was analyzed by gas chromatography and was found to yield cyclohexanon, adipic acid and glutaric acid in 1%, 42% and 13% yields, respectively, at 79% conversion of cyclohexane.
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