1: 96 percent / 0.1N HCl / 0.17 h / 60 °C 2: 82 percent / Br2, sodium acetate / acetic acid / 1 h / Ambient temperature 3: 57 percent / 30 h / 140 °C View Scheme

n-butyllithium; hydrogen sulfide in tetrahydrofuran; hexane

1: With 3-chloro-benzenecarboperoxoic acid in dichloromethane Baeyer-Villiger reaction; 11 h; Heating; 2: With triethylamine in methanol T=20°C; 2 h;

piperidine in ethanol T=20°C;

potassium hydroxide T=100°C;

1: m-chloroperoxybenzoic acid / CHCl3 / 0.75 h / Heating 2: 8.949 g / aq. hydrochloric acid / methanol / 0.5 h / Ambient temperature 3: 93 percent / anhydrous potassium carbonate / acetone / 12 h / Ambient temperature 4: 1.) 1.5 M methyl lithium / 1.) ethyl ether, 0 deg C, 15 min; 2.) 0 deg C, 30 min View Scheme

1: permanganate 2: NaOH-solution; copper / 200 °C 3: perchloric acid View Scheme

1: copper-powder; methanol. KOH 2: aqueous formaldehyde; methanol. KOH 3: SOCl2 / Erwaermen des Reaktionsprodukts mit NaCN in wss. Aceton View Scheme

1: 31 percent / boron trifluoride etherate; sodium cyanoborohydride / tetrahydrofuran / 10 h / Heating 2: 16 percent / lithium / tetrahydrofuran / 1 h / sonication 3: 90 percent / PCC; silica gel / CH2Cl2 / 3 h / 20 °C 4: 90 percent / tetrahydrofuran / 2 h / sonication 5: 97 percent / hydrogen / Pd-CaCO3 / ethanol / 24 h / 20 °C 6: 85 percent / PCC; silica gel / CH2Cl2 / 30 h / 20 °C 7: 75 percent / sodium borohydride / methanol / 1.5 h / cooling 8: 28 percent / propionic acid / 48 h / 180 °C 9: 80 percent / Cl2(PCy3)2Ru=CHPh / CH2Cl2 / 6 h / 20 °C 10: 99 percent / hydrogen / Pd on activated C / ethanol / 3 h / 20 °C / 760 Torr 11: 98 percent / LiAlH4 / diethyl ether / 1 h / 0 °C 12: 89 percent / PCC; silica gel / CH2Cl2 / 0.5 h / 20 °C 13: 77 percent Turnov. / (Ph3P)3RhCl / benzene / 20 h / 120 - 130 °C View Scheme

sodium tetrahydroborate in methanol T=0°C;