UV irradiation of acetonitrile solutions of 1,3-dimethyladamantane in air in the presence of catalytic amounts of different complex compounds of nickel and chromium, iron, molybdenum and rhodium in a low degree of oxidation leads, in the general case, to the formation of 1,3-dimethyladamantan-5-ol, ketones, secondary alcohols, keto alcohols, diketones, diols and tertiary alcohols - products of possible structural rearrangement of 1,3-dimethyladamantane into dimethylprotoadamantane. The yield and composition of the oxidation products are influenced by the nature and concentration of the catalyst, the addition of reducing agents (hydroquinone, ferrocene and zinc in acetic acid) and the reaction time. The highest conversion of 1,3-dimethyladamantane (about 40 and 50% respectively) is observed in the presence of molybdenum and iron compounds containing tris(pyrazolyl)borate and hydrogen ligands, which direct the oxidation reaction mainly by secondary carbon atoms. Ni/Cr, Rh and Fe complexes, which have no hydrogen ligands, promote the oxidation primarily of tertiary carbon atoms.