nickel in tetrahydrofuran T=20°C; Reduction; 0.25 h;

hydrogen; nickel T=65°C;

hydrogen; palladium on activated charcoal in ethanol T=28.9°C; P=1575.1 Torr; 0.115 h;

sodium dichromate; sulfuric acid in water; acetic acid; benzene Ambient temperature;

hydrogen; Catalyst M-Chromium oxide; nickel in ethanol T=22°C; P=3800 Torr; flow system, oth. temperature, oth. pressure; Product distribution;

9-borabicyclo[3.3.1]nonane dimer in tetrahydrofuran 4 h; Ambient temperature;

hydrogen; palladium on activated charcoal in ethanol T=28.9°C; P=825.07 Torr; var. temp (261-318 K), var. pressure (0.11-0.53 MPa), var. solv.: MeOH, AcOH, i-PrOH, cyclohexane; Product distributionKineticsThermodynamic data;

2: 56 percent / LiI*2H2O, 2,4,6-collidine / 19 h / Heating 3: 1.) O3; 2.) NaBH4 / methanol; 1.) -50 deg C, 0.25 h; 2.) -30 deg C, 1 h 4: pyridine / 18 h / Ambient temperature 5: 81 percent / CrO3 / pyridine; CH2Cl2 / 1.5 h / Ambient temperature 6: 1.) 1.6 M n-BuLi / 1.) Et2O, room temp., 3 h; 2.) THF, reflux, 4 h 7: 71 percent / Na, liq. NH3 / tetrahydrofuran / 0.5 h 8: 75 percent / pyridine / 48 h / -20 °C 9: 90 percent / dibenzo-18-crown-6 / acetonitrile / a) room temp., 1 h; b) reflux, 18 h 10: tetrahydrofuran 11: 68 percent / 1 N HCl / Heating View Scheme

hydrogen fluoride in acetonitrile T=20°C; 0.5 h;

1: 75 percent / pyridine / 48 h / -20 °C 2: 90 percent / dibenzo-18-crown-6 / acetonitrile / a) room temp., 1 h; b) reflux, 18 h 3: tetrahydrofuran 4: 68 percent / 1 N HCl / Heating View Scheme