[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)C2=CC=CC=C2C1=O.S(=O)=O.O=O>[O-][V]([O-])([O-])=O.[Na+].[Na+].[Na+].C/C(/O)=C\C(C)=O.C/C(/O)=C\C(C)=O.O=[V].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]2A mixture of 2 mmol of adamantane, 0.2 mmol of N-hydroxyphthalimide, 0.01 mmol of vanadyl acetylacetonato [VO(acac) 2 ], and 5 ml of acetic acid was stirred at 60° C. in a sulfur dioxide (SO2) (0.5 atm) and oxygen (0.5 atm) atmosphere for 1 hour. A gas chromatographic analysis of a reaction mixture revealed that the conversion rate of adamantane was 91% and that a trace amount of 2-adamantanone was formed. The reaction mixture was extracted with water, was neutralized with an aqueous sodium hydroxide solution, and was adjusted to weak acidity with hydrochloric acid. An aqueous benzyl isothiourea hydrochloride solution in large excess was then added to the mixture to separate S-benzyl thiuronium salt of 1-adamantanesulfonic acid. The yield of this compound was 32%.
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