[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH:11]N1C(=O)N(O)C(=O)N(O)[C:13]1=[O:22].[O:23]=O>C(O)(=O)C>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[C:2]1=[O:11])[CH2:8]2.[C:13]12([OH:22])[CH2:9][CH:3]3[CH2:4][CH:5]([CH2:10][CH:1]([CH2:2]3)[CH2:8]1)[CH2:6]2.[C:13]12([OH:22])[CH2:9][CH:7]3[CH2:6][CH:5]([CH2:10][C:1]([OH:23])([CH2:8]3)[CH2:2]1)[CH2:4]2A mixture of 1.00 g of adamantane, 0.026 g of hexahydro-1,3,5-trihydroxy-1,3,5-triazine-2,4,6-trione (2% by mole relative to adamantane), 9.0 g of acetic acid and 0.003 g of acetylacetonatovanadium(III) was stirred at 85° C. in an atmosphere of oxygene gas (1 atm=0.1 MPa) for 6 hours. The resulting product in the reaction mixture was analyzed by gas chromatography and was found to yield 2-adamantanon, 1-adamantanol and 1,3-adamantanediol in 3%, 27% and 4% yields, respectively, at 41% conversion of adamantane.
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