1: 100 percent / H2O / 1.5 h 2: 1.) MeI / 1.) DMF, from 0 deg C to RT, 35 min, 2.) DMF, from 0 deg C to RT, 70 min View Scheme

Mn(5,10,15,20-tetrakis(4-chlorophenyl)porphyrin)Cl; oxygen; sodium hydroxide in methanol T=64.84°C; P=750.075 Torr; 3.5 h; Catalytic behavior; Reagent/catalystSolventTimeTemperature;

1.1: 95 percent / K2CO3 / acetone / 6 h / Heating 2.1: 90 percent / 24 h / 180 °C 3.1: 95 percent / KOH / methanol / 10 h / Heating 4.1: 96 percent / sodium hydroxyde / H2O / 1 h / Heating 5.1: NaHCO3; ozone / methanol; CH2Cl2 / 0.22 h / -70 °C 5.2: 80 percent / dimethyl sulfide / methanol; CH2Cl2 / 8 h / 20 °C 6.1: Mg; iodine / diethyl ether 6.2: 88 percent / diethyl ether / 3 h / 20 °C 7.1: 96 percent / PCC; silica gel / CH2Cl2 / 2 h / 20 °C 8.1: sodium hydride / tetrahydrofuran; various solvent(s) / 0.67 h / 20 °C 8.2: tetrahydrofuran; various solvent(s) / 10 h / 20 °C 8.3: 91 percent / tetrahydrofuran; various solvent(s) / 0.5 h / 180 °C 9.1: 90 percent / tetrahydrofuran / 2 h / sonication 10.1: 97 percent / hydrogen / Pd-CaCO3 / ethanol / 24 h / 20 °C 11.1: 85 percent / PCC; silica gel / CH2Cl2 / 30 h / 20 °C 12.1: 75 percent / sodium borohydride / methanol / 1.5 h / cooling 13.1: 28 percent / propionic acid / 48 h / 180 °C 14.1: 80 percent / Cl2(PCy3)2Ru=CHPh / CH2Cl2 / 6 h / 20 °C 15.1: 99 percent / hydrogen / Pd on activated C / ethanol / 3 h / 20 °C / 760 Torr 16.1: 98 percent / LiAlH4 / diethyl ether / 1 h / 0 °C 17.1: 89 percent / PCC; silica gel / CH2Cl2 / 0.5 h / 20 °C 18.1: 77 percent Turnov. / (Ph3P)3RhCl / benzene / 20 h / 120 - 130 °C View Scheme

1: 91 percent / K2CO3 / acetone / 4 h / Heating 2: 95 percent / NaBH4 / methanol / 0 °C 3: 67 percent / PPh3; CCl4 / toluene / 7 h / Heating View Scheme

1: glacial acetic acid; bromine 2: aq.-ethanolic NaOH View Scheme