sodium amalgam in methanol

tert.-butylhydroperoxide; sodium hydroxide; selenium(IV) oxide in dichloromethane; water; tert-butyl alcohol

1: 1.) NaH / 1.) THF, RT, 1.5 h, 2.) THF, 20 h 2: 84 percent / NaOAc, AcOH / 16 h / 50 °C 3: 92 percent / Ac2O, pyridine / 15 h / Ambient temperature 4: 97 percent / aq.OsO4, KIO4 / tetrahydrofuran; H2O / 16 h / Ambient temperature 5: 85 percent / 90percent H2O2, trifluoroacetic anhydride, KH2PO4 / CH2Cl2 / 0 °C 6: cation exchange resin AG 50W-X4 / ethanol / 50 °C 7: NaOEt / ethanol / 2 h / Ambient temperature 8: 95 percent / imidazole / dimethylformamide / Ambient temperature 9: 81 percent / (Ph2)S<OC(CF3)2Ph>2 / CCl4 / 0.25 h 10: 88 percent / 9-fluorenone / various solvent(s) / 0.5 h / Irradiation 11: 92 percent / diisobutylaluminium hydride / toluene / 0.5 h / -78 °C 12: 91 percent / N-chlorosuccinimide, dimethyl sulfide / CH2Cl2 / 0.5 h / -20 °C 13: 2.) 5percent H2O2 / 1.) THF, -70 deg C, 2.) CH2Cl2, 1 h 14: 1.) n-BuLi / 1.) THF, n-hexane, -78 deg C, 5 min, 2.) THF, n-hexane, -78 deg C, 2 h View Scheme

1: 95 percent / imidazole / dimethylformamide / Ambient temperature 2: 81 percent / (Ph2)S<OC(CF3)2Ph>2 / CCl4 / 0.25 h 3: 88 percent / 9-fluorenone / various solvent(s) / 0.5 h / Irradiation 4: 92 percent / diisobutylaluminium hydride / toluene / 0.5 h / -78 °C 5: 91 percent / N-chlorosuccinimide, dimethyl sulfide / CH2Cl2 / 0.5 h / -20 °C 6: 2.) 5percent H2O2 / 1.) THF, -70 deg C, 2.) CH2Cl2, 1 h 7: 1.) n-BuLi / 1.) THF, n-hexane, -78 deg C, 5 min, 2.) THF, n-hexane, -78 deg C, 2 h View Scheme

1: 84 percent / NaOAc, AcOH / 16 h / 50 °C 2: 92 percent / Ac2O, pyridine / 15 h / Ambient temperature 3: 97 percent / aq.OsO4, KIO4 / tetrahydrofuran; H2O / 16 h / Ambient temperature 4: 85 percent / 90percent H2O2, trifluoroacetic anhydride, KH2PO4 / CH2Cl2 / 0 °C 5: cation exchange resin AG 50W-X4 / ethanol / 50 °C 6: NaOEt / ethanol / 2 h / Ambient temperature 7: 95 percent / imidazole / dimethylformamide / Ambient temperature 8: 81 percent / (Ph2)S<OC(CF3)2Ph>2 / CCl4 / 0.25 h 9: 88 percent / 9-fluorenone / various solvent(s) / 0.5 h / Irradiation 10: 92 percent / diisobutylaluminium hydride / toluene / 0.5 h / -78 °C 11: 91 percent / N-chlorosuccinimide, dimethyl sulfide / CH2Cl2 / 0.5 h / -20 °C 12: 2.) 5percent H2O2 / 1.) THF, -70 deg C, 2.) CH2Cl2, 1 h 13: 1.) n-BuLi / 1.) THF, n-hexane, -78 deg C, 5 min, 2.) THF, n-hexane, -78 deg C, 2 h View Scheme

1: 2.) 5percent H2O2 / 1.) THF, -70 deg C, 2.) CH2Cl2, 1 h 2: 1.) n-BuLi / 1.) THF, n-hexane, -78 deg C, 5 min, 2.) THF, n-hexane, -78 deg C, 2 h View Scheme

1: 97 percent / aq.OsO4, KIO4 / tetrahydrofuran; H2O / 16 h / Ambient temperature 2: 85 percent / 90percent H2O2, trifluoroacetic anhydride, KH2PO4 / CH2Cl2 / 0 °C 3: cation exchange resin AG 50W-X4 / ethanol / 50 °C 4: NaOEt / ethanol / 2 h / Ambient temperature 5: 95 percent / imidazole / dimethylformamide / Ambient temperature 6: 81 percent / (Ph2)S<OC(CF3)2Ph>2 / CCl4 / 0.25 h 7: 88 percent / 9-fluorenone / various solvent(s) / 0.5 h / Irradiation 8: 92 percent / diisobutylaluminium hydride / toluene / 0.5 h / -78 °C 9: 91 percent / N-chlorosuccinimide, dimethyl sulfide / CH2Cl2 / 0.5 h / -20 °C 10: 2.) 5percent H2O2 / 1.) THF, -70 deg C, 2.) CH2Cl2, 1 h 11: 1.) n-BuLi / 1.) THF, n-hexane, -78 deg C, 5 min, 2.) THF, n-hexane, -78 deg C, 2 h View Scheme

1: 85 percent / 90percent H2O2, trifluoroacetic anhydride, KH2PO4 / CH2Cl2 / 0 °C 2: cation exchange resin AG 50W-X4 / ethanol / 50 °C 3: NaOEt / ethanol / 2 h / Ambient temperature 4: 95 percent / imidazole / dimethylformamide / Ambient temperature 5: 81 percent / (Ph2)S<OC(CF3)2Ph>2 / CCl4 / 0.25 h 6: 88 percent / 9-fluorenone / various solvent(s) / 0.5 h / Irradiation 7: 92 percent / diisobutylaluminium hydride / toluene / 0.5 h / -78 °C 8: 91 percent / N-chlorosuccinimide, dimethyl sulfide / CH2Cl2 / 0.5 h / -20 °C 9: 2.) 5percent H2O2 / 1.) THF, -70 deg C, 2.) CH2Cl2, 1 h 10: 1.) n-BuLi / 1.) THF, n-hexane, -78 deg C, 5 min, 2.) THF, n-hexane, -78 deg C, 2 h View Scheme

1: 81 percent / (Ph2)S<OC(CF3)2Ph>2 / CCl4 / 0.25 h 2: 88 percent / 9-fluorenone / various solvent(s) / 0.5 h / Irradiation 3: 92 percent / diisobutylaluminium hydride / toluene / 0.5 h / -78 °C 4: 91 percent / N-chlorosuccinimide, dimethyl sulfide / CH2Cl2 / 0.5 h / -20 °C 5: 2.) 5percent H2O2 / 1.) THF, -70 deg C, 2.) CH2Cl2, 1 h 6: 1.) n-BuLi / 1.) THF, n-hexane, -78 deg C, 5 min, 2.) THF, n-hexane, -78 deg C, 2 h View Scheme

1: cation exchange resin AG 50W-X4 / ethanol / 50 °C 2: NaOEt / ethanol / 2 h / Ambient temperature 3: 95 percent / imidazole / dimethylformamide / Ambient temperature 4: 81 percent / (Ph2)S<OC(CF3)2Ph>2 / CCl4 / 0.25 h 5: 88 percent / 9-fluorenone / various solvent(s) / 0.5 h / Irradiation 6: 92 percent / diisobutylaluminium hydride / toluene / 0.5 h / -78 °C 7: 91 percent / N-chlorosuccinimide, dimethyl sulfide / CH2Cl2 / 0.5 h / -20 °C 8: 2.) 5percent H2O2 / 1.) THF, -70 deg C, 2.) CH2Cl2, 1 h 9: 1.) n-BuLi / 1.) THF, n-hexane, -78 deg C, 5 min, 2.) THF, n-hexane, -78 deg C, 2 h View Scheme