1: 90 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / 1.5 h / Heating; Irradiation 2: 1.85 g / diethyl ether / 8 h View Scheme

in diethyl ether 8 h;

sodium hydroxide; dihydrogen peroxide; diborane 1.) THF, room temperature, 12h, 2a.) 5 deg C, 2 h, 2b.) reflux , 8h; Yield given. Multistep reaction;

1: 1.) diborane, sodium hydroxide, 2.) H2O2 / 1.) THF, room temperature, 12h, 2a.) 5 deg C, 2 h, 2b.) reflux , 8h 2: 82 percent / pyridinium chlorochromate / CH2Cl2 / 3 h View Scheme

1: 1.) diborane, sodium hydroxide, 2.) H2O2 / 1.) THF, room temperature, 12h, 2a.) 5 deg C, 2 h, 2b.) reflux , 8h 2: 82 percent / pyridinium chlorochromate / CH2Cl2 / 3 h 3: 62 percent / AgNO3, NaOH / tetrahydrofuran; H2O / 2 h / Ambient temperature View Scheme

1: 1.) diborane, sodium hydroxide, 2.) H2O2 / 1.) THF, room temperature, 12h, 2a.) 5 deg C, 2 h, 2b.) reflux , 8h 2: 82 percent / pyridinium chlorochromate / CH2Cl2 / 3 h 3: 62 percent / AgNO3, NaOH / tetrahydrofuran; H2O / 2 h / Ambient temperature 4: 1.8 g / oxalyl chloride / CH2Cl2 / 3 h / Ambient temperature 5: AlCl3 / CS2 / 1.) 0 deg C , 1h, 2.) reflux , 30 min 6: 0.8 g / lithium aluminumhydride / tetrahydrofuran / 1 h / Ambient temperature 7: 72 percent / HCl / acetic acid / 1 h / 90 °C View Scheme