Dimanganese decacarbonyl

Vinylidene fluoride (VDF, Dyneon GmbH, Burgkirchen a.d.Alz, Germany, 99.5%), styrene (S, Sigma-Aldrich, Taufkirchen, Germany, 99.5%), methyl methacrylate (MMA, Sigma-Aldrich, Taufkirchen, Germany, 99%), di-tert-butylperoxide (DTBP, Merck, Darmstadt, Germany, 98%), 1-iodoperfluorohexane (ABCR, Karlsruhe, Germany, 99%), 1,4-diiodooctafluorobutane (Dyneon GmbH, Burgkirchen a.d.Alz, Germany), dimanganese decacarbonyl (Sigma-Aldrich, Taufkirchen, Germany, 98%), methanol (95%), hydrochloric acid (37%), N,N-dimethyl acetamide (DMAc, Acros, Geel, Belgium, 99%), ammonium 4,8-dioxa-3H-perfluorononanoate (Dyneon, GmbH, Burgkirchen a.d.Alz, Germany), ammonium peroxydisulfate (Fluka, Honeywell, Hannover, Germany, ≥98.0%), carbon dioxide (Air Liquide, Paris, France, 99.8%), N,N-dimethylformamide-d₇ (Deutero GmbH, Kastellaun, Germany, 99.5%), and acetone-d₆ (Deutero GmbH, Kastellaun, Germany, 99.8%) were used as received.

Reagents were purchased from the following sources: (S)-warfarin, 7-ethoxycoumarin, and dimanganese decacarbonyl (Sigma-Aldrich, St. Louis, MO, USA); (S)-7-hydroxywarfarin (BD Gentest, Woburn, MA, USA); tolbutamide (FUJIFILM Wako Pure Chemical Corporation, Osaka, Japan); 4-hydroxytolbutamide and 4-hydroxytolbutamide-d9 (Toronto Research Chemicals, North York, ON, Canada); oxidized β-nicotinamide-adenine dinucleotide reduced form and β-nicotinamide-adenine dinucleotide phosphate reduced form (NADPH; Oriental Yeast, Tokyo, Japan); polyclonal anti-human CYP2C9 antibody (cat. no. ab4236; Abcam, Cambridge, UK); horseradish peroxidase (HRP)-conjugated goat anti-rabbit IgG (ProteinSimple, Tokyo, Japan); and sodium cyanide and cytochrome c from horse hearts (Nacalai Tesque, Kyoto, Japan). All other chemicals and reagents were of the highest commercially available quality.

Manganese(II) chloride (reagent grade, ≥99%), tetramethylammonium hydroxide pentahydrate, sulfur powder (99.98%), dimanganese decacarbonyl (98%), oleic acid (90%), stearic acid (99%), oleylamine (technical grade, 70%), dodecylamine (98%), hexadecylamine (90%), octadecylamine (≥99%), dodecanthiol (98%), oleylalcohol (≥85%), tryoctylphosphine (97%), and octadecene (purum, ≥95.0%) were purchased from Sigma-Aldrich. stearic acid (99%) was purchased from Calbiochem. All chemicals were used as received without further purification.