Hydroxylation of polycyclic alkanes with molecular oxygen catalyzed by N-hydroxyphthalimide (NHPI) combined with transition metal salts

Adamantanes were successfully converted into the corresponding mono- and dihydroxy adamantanes with molecular oxygen in the presence of N-hydroxyphthalimide (NHPI) combined with cobalt salts under mild conditions. For example, exposure of adamantane under oxygen atmosphere in the presence of NHPI (10 mol%) and Co(acac)(2) (0.5 mol%) in acetic acid at 75 degrees C for 6 h afforded adamantan-1-ol (43 %) and adamantane-1,3-diol (40 %) along with adamantan-2-one (8 %) in 93 % conversion. Similarly, 1,3-dimethyladamantane produced 3,5-dimethyladamantan-1-ol (47 %) and 5,7-dimethyladamantane-1,3-diol (37 %). Copyright (C) 1996 Elsevier Science Ltd