1: 88 percent / ammonia / methanol / 36 h / 110 °C 2: 77 percent / palladium oxide, cyclohexene / ethanol / 1.) 18 h; 2.) reflux, 2.5 h View Scheme

1: 88 percent / ammonia / methanol / 36 h / 110 °C 2: 77 percent / palladium oxide, cyclohexene / ethanol / 1.) 18 h; 2.) reflux, 2.5 h 3: 82 percent / bromine-water / 22 °C / pH=4.3 View Scheme

1: 88 percent / ammonia / methanol / 36 h / 110 °C 2: 77 percent / palladium oxide, cyclohexene / ethanol / 1.) 18 h; 2.) reflux, 2.5 h 3: 14 percent / triphenylphosphine, lithium azide, carbon tetrabromide / dimethylformamide / 24 h / Ambient temperature View Scheme

1: 88 percent / ammonia / methanol / 36 h / 110 °C 2: 77 percent / palladium oxide, cyclohexene / ethanol / 1.) 18 h; 2.) reflux, 2.5 h 3: 53 percent / triphenylphosphine, lithium azide, carbon tetrabromide / dimethylformamide / 24 h / Ambient temperature View Scheme

1: 88 percent / ammonia / methanol / 36 h / 110 °C 2: 77 percent / palladium oxide, cyclohexene / ethanol / 1.) 18 h; 2.) reflux, 2.5 h 3: 14 percent / triphenylphosphine, lithium azide, carbon tetrabromide / dimethylformamide / 24 h / Ambient temperature 4: 90 percent / 5percent Pd/C, H2 / ethanol / 18 h / Ambient temperature View Scheme

1: 88 percent / ammonia / methanol / 36 h / 110 °C 2: 77 percent / palladium oxide, cyclohexene / ethanol / 1.) 18 h; 2.) reflux, 2.5 h 3: 53 percent / triphenylphosphine, lithium azide, carbon tetrabromide / dimethylformamide / 24 h / Ambient temperature 4: 52 percent / 5percent Pd/C, H2 / aq. ethanol / 2 h / Ambient temperature View Scheme

1: 87 percent / 5percent Pd/C, H2, anhydrous sodium acetate / ethanol / 18 h / 2068.6 Torr / Ambient temperature 2: 87 percent / 1N BCl3 / CH2Cl2 / 1.) -78 deg C, 3 h; 2.) r.t., 1 h View Scheme

boron trichloride in dichloromethane 1.) -78 deg C, 3 h; 2.) r.t., 1 h;