Acetic Acid → Adamantanone

Participants

Reaction Steps

To 25 ml of acetic acid were added 10 mmol of adamantane, 1 mmol of N-hydroxyphthalimide and 0.2 mmol of phosphovanadotungstic acid (PV4W8O40.30H2), and the resultant mixture (pH 1.9) was stirred under an oxygen atmosphere at a temperature of 75° C. for 6 hours. The products in the reaction mixture were analyzed by gas chromatography, and, as a result, adamantane was converted into adamantanone (yield 32%) and 1-hydroxyadamantanone (yield 16%) with a conversion of 79%. Incidentally, excepting the above, 1-adamantanol (yield 15%), 1,3-adamantanediol (yield 8%) and other products (polyketone such as adamantanedione) (yield 8%) were formed.

Provenance & Evidence