triethylsilane in trifluoroacetic acid 48 h; Ambient temperature;

1: 2.) 2 M aq. Na2CO3 / 1.) Pd(PPh3)4 / 1.) EtOH, DME, 10 min, 2.) reflux, 20 h 2: 76 percent / NBS / benzoyl peroxide / CCl4 / 36 h / Heating 3: AgNO3 / dioxane; H2O / 18 h / Ambient temperature 4: aq. KOH / dioxane / 20 h / Ambient temperature 5: 98 percent / aq. KMnO4 / acetone / 4 h / Ambient temperature 6: 88 percent / polyphosphoric acid / 5 h / 160 °C 7: 73 percent / Et3SiH / trifluoroacetic acid / 48 h / Ambient temperature View Scheme

1: 76 percent / NBS / benzoyl peroxide / CCl4 / 36 h / Heating 2: AgNO3 / dioxane; H2O / 18 h / Ambient temperature 3: aq. KOH / dioxane / 20 h / Ambient temperature 4: 98 percent / aq. KMnO4 / acetone / 4 h / Ambient temperature 5: 88 percent / polyphosphoric acid / 5 h / 160 °C 6: 73 percent / Et3SiH / trifluoroacetic acid / 48 h / Ambient temperature View Scheme

1: 2.) 2 M aq. Na2CO3 / 1.) Pd(PPh3)4 / 1.) EtOH, DME, 10 min, 2.) reflux, 20 h 2: 76 percent / NBS / benzoyl peroxide / CCl4 / 36 h / Heating 3: AgNO3 / dioxane; H2O / 18 h / Ambient temperature 4: aq. KOH / dioxane / 20 h / Ambient temperature 5: 98 percent / aq. KMnO4 / acetone / 4 h / Ambient temperature 6: 88 percent / polyphosphoric acid / 5 h / 160 °C 7: 73 percent / Et3SiH / trifluoroacetic acid / 48 h / Ambient temperature View Scheme

sodium tetrahydroborate in methanol

1: 88 percent / polyphosphoric acid / 5 h / 160 °C 2: 73 percent / Et3SiH / trifluoroacetic acid / 48 h / Ambient temperature View Scheme

1: 98 percent / aq. KMnO4 / acetone / 4 h / Ambient temperature 2: 88 percent / polyphosphoric acid / 5 h / 160 °C 3: 73 percent / Et3SiH / trifluoroacetic acid / 48 h / Ambient temperature View Scheme

1: AgNO3 / dioxane; H2O / 18 h / Ambient temperature 2: aq. KOH / dioxane / 20 h / Ambient temperature 3: 98 percent / aq. KMnO4 / acetone / 4 h / Ambient temperature 4: 88 percent / polyphosphoric acid / 5 h / 160 °C 5: 73 percent / Et3SiH / trifluoroacetic acid / 48 h / Ambient temperature View Scheme

hydrogen azide; chloroform; sulfuric acid

1: hydrazoic acid; chloroform; concentrated sulfuric acid 2: iron View Scheme