N-bromosuccinmide; meta-chloroperoxybenzoic acid in tetrachloromethane 1.5 h; HeatingIrradiation;

in diethyl ether 8 h;

1: 1.85 g / diethyl ether / 8 h 2: 1.) diborane, sodium hydroxide, 2.) H2O2 / 1.) THF, room temperature, 12h, 2a.) 5 deg C, 2 h, 2b.) reflux , 8h View Scheme

1: 1.85 g / diethyl ether / 8 h 2: 1.) diborane, sodium hydroxide, 2.) H2O2 / 1.) THF, room temperature, 12h, 2a.) 5 deg C, 2 h, 2b.) reflux , 8h 3: 82 percent / pyridinium chlorochromate / CH2Cl2 / 3 h View Scheme

1: 1.85 g / diethyl ether / 8 h 2: 1.) diborane, sodium hydroxide, 2.) H2O2 / 1.) THF, room temperature, 12h, 2a.) 5 deg C, 2 h, 2b.) reflux , 8h 3: 82 percent / pyridinium chlorochromate / CH2Cl2 / 3 h 4: 62 percent / AgNO3, NaOH / tetrahydrofuran; H2O / 2 h / Ambient temperature View Scheme

1: 1.85 g / diethyl ether / 8 h 2: 1.) diborane, sodium hydroxide, 2.) H2O2 / 1.) THF, room temperature, 12h, 2a.) 5 deg C, 2 h, 2b.) reflux , 8h 3: 82 percent / pyridinium chlorochromate / CH2Cl2 / 3 h 4: 62 percent / AgNO3, NaOH / tetrahydrofuran; H2O / 2 h / Ambient temperature 5: 1.8 g / oxalyl chloride / CH2Cl2 / 3 h / Ambient temperature 6: AlCl3 / CS2 / 1.) 0 deg C , 1h, 2.) reflux , 30 min 7: 0.8 g / lithium aluminumhydride / tetrahydrofuran / 1 h / Ambient temperature 8: 72 percent / HCl / acetic acid / 1 h / 90 °C View Scheme

1,3,5,7-tetra-azatricyclo[5.1.1.13,5]decane in ethanol 4 h; Heating;