INTERACTION OF MOLECULAR-OXYGEN WITH AMINOPHENOLS MEDIATED BY COPPER METAL AND COPPER-COMPOUNDS

Several copper compounds (Cu, Cu2O, CuO, CuCl and CuCl2) have been used as catalysts for the oxidation of 2-, 3- and 4-aminophenol with O2 at 25-degrees-C; a comparison of their activities was made through kinetic determinations. The oxidation of 2-aminophenol selectively produced 2-amino-phenoxazin-3-one (1), whereas the oxidation products of 3- and 4-aminophenol were two new compounds, 2-amino-5 [(3-hydroxyphenyl)amino]-2,5-cyclohexadiene-1,4-dione (3) and 3-[(4-hydroxyphenyl)amino]-4-[(2-amino-5-hydroxy)phenyl]-6-[(4-hydroxyphenyl)imino]-2, 4-cyclohexadien-1-one (2).