[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][N:12]1C(=O)C2=CC=CC=C2C1=O.[N+]([O-])=[O:24].FC(C1C=CC=CC=1)(F)F.O=O>>[N+:12]([C:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2)([O-:11])=[O:24].[C:1]12([OH:11])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2Into a flask, 1 mmole of adamantane, 0.05 mmole of N-hydroxyphthalimide, 15 mmole of nitrogen dioxide (NO2) and 3 ml of trifluoromethylbenzene were added and stirred for 5 hours at 60° C. in an atmosphere of oxygen. The reaction products were analyzed by gas chromatography, and, as a result, the conversion of adamantane was 79%, and nitroadamantane (yield 57%), adamantanol (yield 6%) and adamantanone (yield 4%) were formed.
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