Oxygen → Adamantanone

HRID 1857079Notes

Reaction equation

HRID 1857079 reaction equation
[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.C(OO)(C)(C)C.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]2

Participants

9

Reactant 5

HCID 977OxygenHCID 1119Sulfur DioxideHCID 6410tert-Butyl hydroperoxideHCID 9238Adamantane2×HCID 10665N-Hydroxyphthalimide

Product 1

HCID 64151AdamantanoneYield 3%

Reagents, catalysts & solvents 3

HCID 61671Sodium orthovanadateCatalystHCID 16217092Bis(2,4-pentanedionato)vanadium(IV) OxideCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2 mmol of adamantane, 0.2 mmol of N-hydroxyphthalimide, 0.01 mmol of vanadyl acetylacetonato [VO(acac) 2 ], 0.02 mmol of TBHP (t-butyl hydroperoxide), and 5 ml of acetic acid was stirred at 25° C. in a sulfur dioxide (SO2) (0.5 atm) and oxygen (0.5 atm) atmosphere for 20 hours. A gas chromatographic analysis of a reaction mixture revealed that the conversion rate of adamantane was 53% and that 2-adamantanone was formed in a yield of 3%. 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 40%.

Sources & evidence

ORD record
ord-4342e3091bc0496f95c778676d4a8e0d
Source dataset
uspto-grants-2000_11
Patent number
US06143924

Reaction notes

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