boron tribromide in dichloromethane; water

1: 91 percent / cyclohexene / 10percent Pd/C / propan-2-ol / 8 h / Heating 2: 1.) NaNO2, aq. H2SO4, 2.) aq. H2SO4 / 1.) from 0 deg C to 5 deg C, 2.) reflux, 30 min View Scheme

1: 78 percent / pyridine / tetrahydrofuran / 3 h / Ambient temperature 2: 91 percent / cyclohexene / 10percent Pd/C / propan-2-ol / 8 h / Heating 3: 1.) NaNO2, aq. H2SO4, 2.) aq. H2SO4 / 1.) from 0 deg C to 5 deg C, 2.) reflux, 30 min View Scheme

1: 78 percent / pyridine / tetrahydrofuran / 3 h / Ambient temperature 2: 91 percent / cyclohexene / 10percent Pd/C / propan-2-ol / 8 h / Heating 3: 1.) NaNO2, aq. H2SO4, 2.) aq. H2SO4 / 1.) from 0 deg C to 5 deg C, 2.) reflux, 30 min View Scheme

phosphorus pentoxide in toluene 3 h; Heating;

sulfuric acid; sodium nitrite 1.) from 0 deg C to 5 deg C, 2.) reflux, 30 min; Yield given. Multistep reaction;