hydrogen; platinum(IV) oxide in tetrahydrofuran P=1034.3 Torr;

1: 93 percent / AlCl3 / CS2 / 3 h / Heating 2: 98 percent / NaBH4 / ethanol / 2 h / 25 °C 3: 92 percent / p-toluenesulfonic acid*H2O / benzene / 1 h / Heating 4: 99 percent / NiCl2<dppp>2 / diethyl ether / Heating 5: 97 percent / H2 / PtO2 / tetrahydrofuran / 1034.3 Torr View Scheme

1: 89 percent / KOH / acetic acid; H2O; tetrahydrofuran / 12 h / 25 °C 2: 81 percent / 165 °C 3: thionyl chloride / 0.75 h / Heating 4: 93 percent / AlCl3 / CS2 / 3 h / Heating 5: 98 percent / NaBH4 / ethanol / 2 h / 25 °C 6: 92 percent / p-toluenesulfonic acid*H2O / benzene / 1 h / Heating 7: 99 percent / NiCl2<dppp>2 / diethyl ether / Heating 8: 97 percent / H2 / PtO2 / tetrahydrofuran / 1034.3 Torr View Scheme

1: 98 percent / NaBH4 / ethanol / 2 h / 25 °C 2: 92 percent / p-toluenesulfonic acid*H2O / benzene / 1 h / Heating 3: 99 percent / NiCl2<dppp>2 / diethyl ether / Heating 4: 97 percent / H2 / PtO2 / tetrahydrofuran / 1034.3 Torr View Scheme

1: thionyl chloride / 0.75 h / Heating 2: 93 percent / AlCl3 / CS2 / 3 h / Heating 3: 98 percent / NaBH4 / ethanol / 2 h / 25 °C 4: 92 percent / p-toluenesulfonic acid*H2O / benzene / 1 h / Heating 5: 99 percent / NiCl2<dppp>2 / diethyl ether / Heating 6: 97 percent / H2 / PtO2 / tetrahydrofuran / 1034.3 Torr View Scheme

1: 81 percent / 165 °C 2: thionyl chloride / 0.75 h / Heating 3: 93 percent / AlCl3 / CS2 / 3 h / Heating 4: 98 percent / NaBH4 / ethanol / 2 h / 25 °C 5: 92 percent / p-toluenesulfonic acid*H2O / benzene / 1 h / Heating 6: 99 percent / NiCl2<dppp>2 / diethyl ether / Heating 7: 97 percent / H2 / PtO2 / tetrahydrofuran / 1034.3 Torr View Scheme

1: 92 percent / p-toluenesulfonic acid*H2O / benzene / 1 h / Heating 2: 99 percent / NiCl2<dppp>2 / diethyl ether / Heating 3: 97 percent / H2 / PtO2 / tetrahydrofuran / 1034.3 Torr View Scheme

1: 99 percent / NiCl2<dppp>2 / diethyl ether / Heating 2: 97 percent / H2 / PtO2 / tetrahydrofuran / 1034.3 Torr View Scheme

1: 64 percent / NaOC2H5 / 3.5 h / Heating 2: 89 percent / KOH / acetic acid; H2O; tetrahydrofuran / 12 h / 25 °C 3: 81 percent / 165 °C 4: thionyl chloride / 0.75 h / Heating 5: 93 percent / AlCl3 / CS2 / 3 h / Heating 6: 98 percent / NaBH4 / ethanol / 2 h / 25 °C 7: 92 percent / p-toluenesulfonic acid*H2O / benzene / 1 h / Heating 8: 99 percent / NiCl2<dppp>2 / diethyl ether / Heating 9: 97 percent / H2 / PtO2 / tetrahydrofuran / 1034.3 Torr View Scheme

tetra-n-propyl-diborane; hydrogen in n-heptane T=200°C; P=75006 Torr; 0.5 h; Product distribution;