Catalytic activity of amines in the oxidation of anthrone

The rate of non-radical oxidation of anthrone with molecular oxygen, catalyzed by aliphatic amines with different substituents, amino acids, aromatic amines, and compounds possessing several basic centers, was measured. The catalytic activity of amines decreases in the series RO(CH₂) _n NH₂ > RNH₂ > morpholine derivatives > RR′N(CH₂) _n NH₂ > guanidine > RR′NH > RR′R″N > 1,4-diazabicyclo2.2.2]octane > amino acids > (R)PhNH₂. A relation was found between proton affinities and structural parameters of the amines and their catalytic activity in the title reaction.