potassium permanganate; water

1.1: Mg; iodine / diethyl ether 1.2: 88 percent / diethyl ether / 3 h / 20 °C 2.1: 96 percent / PCC; silica gel / CH2Cl2 / 2 h / 20 °C 3.1: sodium hydride / tetrahydrofuran; various solvent(s) / 0.67 h / 20 °C 3.2: tetrahydrofuran; various solvent(s) / 10 h / 20 °C 3.3: 91 percent / tetrahydrofuran; various solvent(s) / 0.5 h / 180 °C 4.1: 90 percent / tetrahydrofuran / 2 h / sonication 5.1: 97 percent / hydrogen / Pd-CaCO3 / ethanol / 24 h / 20 °C 6.1: 85 percent / PCC; silica gel / CH2Cl2 / 30 h / 20 °C 7.1: 75 percent / sodium borohydride / methanol / 1.5 h / cooling 8.1: 28 percent / propionic acid / 48 h / 180 °C 9.1: 80 percent / Cl2(PCy3)2Ru=CHPh / CH2Cl2 / 6 h / 20 °C 10.1: 99 percent / hydrogen / Pd on activated C / ethanol / 3 h / 20 °C / 760 Torr 11.1: 98 percent / LiAlH4 / diethyl ether / 1 h / 0 °C 12.1: 89 percent / PCC; silica gel / CH2Cl2 / 0.5 h / 20 °C 13.1: 77 percent Turnov. / (Ph3P)3RhCl / benzene / 20 h / 120 - 130 °C View Scheme