Butanedione → 3,5-Dimethyl-1-adamantanol

Participants

Reaction Steps

A mixture of 3 mmol of 1,3-dimethyladamantane, 9 mmol of biacetyl, 0.0006 mmol of cobalt (II) acetate, and 3 ml of acetic acid was starred at 60° C. under an oxygen atmosphere(1 atm) for 4 hours. Gas chromatographic analysis of products in the reaction mixture demonstrated that 1,3-dimethyladamantane was converted, at a rate of 40%, to 1-acetyl-3,5-dimethyladamantane (yield 8%, selectivity 20%), 1-acetyl-3,5-dimethyl-7-adamantanol (trace), 1,3-dimethyl-5-adamantanol (yield 17%, selectivity 43%), and 1,3-dimethyl-4-adamantanone (yield 5%, selectivity 13%).

Provenance & Evidence