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

Dinucleating hexaazadiphenol macrocyclic ligand [24]RBPyBC forms a dinuclea r iron(II) complex, which reacts with molecular oxygen and catalyzes its in sertion into C-H bond of adamantane in an acetonitrile solvent system conta ining pyridine and in the presence of hydrogen sulfide as a two-electron re ductant. Turnover number, mass balance, and mole ratios of the reaction pro ducts, the 2-adamantanone, 2-adamantanol, and 1-adamantanol vary with respe ct to the amount of the catalyst, O-2, H2S, adamantane, and pyridine. Using the Plackett-Burman experimental design, it is shown that experimental con ditions 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 opt imize catalytic oxidation of adamantane. (C) 2001 Elsevier Science B.V. All rights reserved.