hydrogen; platinum(IV) oxide in methanol Ambient temperature;

1: 45 percent / Heating 2: 1.) n-BuLi / 1.) THF, DMSO, hexane, RT, 30 min, 2.) THF, DMSO, hexane, RT, 3 h 3: 100 percent / H2 / PtO2 / methanol / Ambient temperature View Scheme

1: 100 percent / p-toluenesulfonic acid / CHCl3 2: 45 percent / Heating 3: 1.) n-BuLi / 1.) THF, DMSO, hexane, RT, 30 min, 2.) THF, DMSO, hexane, RT, 3 h 4: 100 percent / H2 / PtO2 / methanol / Ambient temperature View Scheme

1: HBr / heptane / 60 h 2: 100 percent / p-toluenesulfonic acid / CHCl3 3: 45 percent / Heating 4: 1.) n-BuLi / 1.) THF, DMSO, hexane, RT, 30 min, 2.) THF, DMSO, hexane, RT, 3 h 5: 100 percent / H2 / PtO2 / methanol / Ambient temperature View Scheme