1: 81 percent / lithium aluminium hydride / tetrahydrofuran / 1 h / 0 °C 2: 38 percent / phosphorus tribromide, pyridine / 1 h / Ambient temperature 3: 1.) magnesium, ether, 0 deg.C; 2.) ether, room temp., 0.5h 4: 57 percent / m-chloroperbenzoic acid / CH2Cl2 / 3 h / Ambient temperature 5: 96 percent / pyridine / 3 h / 0 °C View Scheme

1: 1.) lithium aluminum hydride, 2.) 15percent NaOH / 1.) Et2O, from 0 deg C to room temp., 2 h., 2.) Et2O, water, 30 min. 2: 87 percent / tributylamine, thionyl chloride / 1 h 3: 1.) magnesium / 1.) THF, reflux, 1.5 h., 2.) benzene, THF, room temp., 2 h. 5: diisobutylaluminum hydride / diethyl ether / 0.5 h / -105 - -95 °C 6: diethyl zinc, O2 / toluene / 0.17 h 7: Celite, pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature 8: benzene / 2.25 h / Ambient temperature View Scheme

ozone in methanol; dichloromethane T=-78°C;

oxygen; copper dichloride; palladium dichloride in ethylene glycol dimethyl ether; water T=80°C; 6 h;

1: 81 percent / lithium aluminium hydride / tetrahydrofuran / 1 h / 0 °C 2: 38 percent / phosphorus tribromide, pyridine / 1 h / Ambient temperature View Scheme

lithium aluminium tetrahydride in tetrahydrofuran T=0°C; 1 h;