hydrogen; palladium on activated charcoal in ethyl acetate P=735.5 Torr; 4 h; Ambient temperature;

1: 25 percent / DDQ / dioxane / 10 h / Heating 2: 8 percent / H2 / Pd-C / ethyl acetate / 4 h / 735.5 Torr / Ambient temperature View Scheme

ammonia; lithium

1: 70 percent / iodoxybenzene, benzeneseleninic anhydride / toluene / 3 h / Heating 2: 87 percent / 2 M LiOH / methanol / 1.5 h / Ambient temperature 3: lithium, liq. ammonia / tetrahydrofuran / 0.33 h / Ambient temperature 4: H+ View Scheme

1: 87 percent / 2 M LiOH / methanol / 1.5 h / Ambient temperature 2: lithium, liq. ammonia / tetrahydrofuran / 0.33 h / Ambient temperature 3: H+ View Scheme

1: 29 percent / DDQ / dioxane / 8 h / Heating 2: 22 percent / Li, liq. NH3 View Scheme

1: 100 percent / ammonia / methanol / 0.5 h / Ambient temperature 2: 70 percent / iodoxybenzene, benzeneseleninic anhydride / toluene / 3 h / Heating 3: 87 percent / 2 M LiOH / methanol / 1.5 h / Ambient temperature 4: lithium, liq. ammonia / tetrahydrofuran / 0.33 h / Ambient temperature 5: H+ View Scheme

1: 86 percent / 60percent perchloric acid / 1.5 h / 50 °C 2: 100 percent / ammonia / methanol / 0.5 h / Ambient temperature 3: 70 percent / iodoxybenzene, benzeneseleninic anhydride / toluene / 3 h / Heating 4: 87 percent / 2 M LiOH / methanol / 1.5 h / Ambient temperature 5: lithium, liq. ammonia / tetrahydrofuran / 0.33 h / Ambient temperature 6: H+ View Scheme

1: lithium, liq. ammonia / tetrahydrofuran / 0.33 h / Ambient temperature 2: H+ View Scheme

Wilkinson's catalyst; hydrogen in ethanol; benzene 25 h; Yield given;