ethanol; palladium(II) hydroxide/carbon in cyclohexene 48 h; Heating / reflux;

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

1: 77 percent / palladium oxide, cyclohexene / ethanol / 1.) 18 h; 2.) reflux, 2.5 h 2: 14 percent / triphenylphosphine, lithium azide, carbon tetrabromide / dimethylformamide / 24 h / Ambient temperature View Scheme

1: 77 percent / palladium oxide, cyclohexene / ethanol / 1.) 18 h; 2.) reflux, 2.5 h 2: 53 percent / triphenylphosphine, lithium azide, carbon tetrabromide / dimethylformamide / 24 h / Ambient temperature View Scheme

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

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