Toward understanding of the synergistic oxidation of adamantane and hydrogen sulfide by molecular oxygen and with a dinuclear iron(II) macrocyclic complex as a catalyst Original Research Article

Dinucleating hexaazadiphenol macrocyclic ligand [24]RBPyBC forms a dinuclear iron(II) complex, which reacts with molecular oxygen and catalyzes its insertion into CH bond of adamantane in an acetonitrile solvent system containing pyridine and in the presence of hydrogen sulfide as a two-electron reductant. Turnover number, mass balance, and mole ratios of the reaction products, the 2-adamantanone, 2-adamantanol, and 1-adamantanol vary with respect to the amount of the catalyst, O2, H2S, adamantane, and pyridine. Using the Plackett–Burman experimental design, it is shown that experimental conditions can be successfully predicted to offer an increase in turnovers or better selectivity of the reaction products. This work provides a practical application of a remarkably simple and effective statistical method to optimize catalytic oxidation of adamantane.