1.1: 87 percent / CBr4; Ph3P / CH2Cl2 / -7 °C 2.1: LiHMDS / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C 2.2: 91 percent / tetrahydrofuran; hexane / 1.5 h / -78 - 50 °C 3.1: 96 percent / hydrogen / Pd/C / ethanol / 4 h / 20 °C / 760 Torr 4.1: NaH / dimethylsulfoxide / 1 h / 0 - 20 °C 4.2: 91 percent / dimethylsulfoxide / 24 h / 75 - 80 °C 5.1: 81 percent / hydrogen; MeOH / Pd/C / triethylamine / 12 h / 20 °C / 760 Torr 6.1: 100 percent / aq. HCl / tetrahydrofuran / 2 h / 20 °C 7.1: n-BuLi / dioxane; hexane / 1 h / 20 °C 7.2: 93 percent / dioxane; hexane / 4 h / 110 °C 8.1: 54 percent / ammonium cerium(IV) nitrate / acetonitrile; H2O / 11 h / -7 - 20 °C / pH 0.7 - 1.3 View Scheme

1.1: 87 percent / CBr4; Ph3P / CH2Cl2 / -7 °C 2.1: LiHMDS / tetrahydrofuran; hexane / 0.5 h / -78 - 0 °C 2.2: 91 percent / tetrahydrofuran; hexane / 1.5 h / -78 - 50 °C 3.1: 96 percent / hydrogen / Pd/C / ethanol / 4 h / 20 °C / 760 Torr 4.1: NaH / dimethylsulfoxide / 1 h / 0 - 20 °C 4.2: 91 percent / dimethylsulfoxide / 24 h / 75 - 80 °C 5.1: 81 percent / hydrogen; MeOH / Pd/C / triethylamine / 12 h / 20 °C / 760 Torr 6.1: 100 percent / aq. HCl / tetrahydrofuran / 2 h / 20 °C 7.1: n-BuLi / dioxane; hexane / 1 h / 20 °C 7.2: 93 percent / dioxane; hexane / 4 h / 110 °C 8.1: 10 percent / ammonium cerium(IV) nitrate / acetonitrile; H2O / 11 h / -7 - 20 °C / pH 0.7 - 1.3 View Scheme

carbon tetrabromide; triphenylphosphine in dichloromethane T=-7°C; Substitution;