n-BuNF in tetrahydrofuran T=45°C; 4 h;

tetrabutyl ammonium fluoride in tetrahydrofuran T=20°C; 2 h;

tetrabutyl ammonium fluoride in tetrahydrofuran T=25°C; Yield given;

1-(9-anthryl)ethanone in methanol-d4 1.5 h; Irradiation;

1-(9-anthryl)ethanone in methanol T=0°C; 2 h; Irradiation;

1: 14.6 g / imidazole / dimethylformamide / 16 h / Ambient temperature 2: 84 percent / diethylamine, CuI, bis<triphenylphosphine>palladium(II) acetate / dimethylformamide / 1.5 h / Ambient temperature 3: 70 percent / tetrabutylammonium fluoride / tetrahydrofuran / 21 h / Ambient temperature 4: 90 percent / H2, quinoline / Lindlar catalyst / methanol; hexane / 0.33 h 5: acetone-d6 / 80.3 °C / var. temp.; kinetics, E(a), ΔG(excit.), ΔH(excit.), ΔS(excit.) View Scheme

1.1: 96 percent / i-Pr2NEt; DMAP / CH2Cl2 / 24 h / 20 °C 2.1: HMDS / tetrahydrofuran / 2 h / -60 °C 2.2: 60 percent / tetrahydrofuran / 17 h / -60 - -5 °C 3.1: t-BuLi / diethyl ether; pentane / 0.5 h / -78 °C 3.2: ZnBr2 / tetrahydrofuran; diethyl ether; pentane / -78 - -10 °C 3.3: 75 percent / Et3N / (Ph3P)4Pd / tetrahydrofuran; diethyl ether; pentane / -40 - 20 °C 4.1: 95 percent / n-Bu4NF / tetrahydrofuran / 2 h / 20 °C View Scheme

1: hydrogen / Pd/BaSO4 / ethanol 2: NaBH4 / ethanol 3: 96 percent / diethyl ether; tetrahydrofuran / Heating 4: pyridine / 0 °C 5: NaI / dimethylformamide; pyridine / 100 °C 6: hydrogen / Pd/C / ethanol / 25 °C 7: EtONa / ethanol / 25 °C 8: 95 percent / m-CPBA / CH2Cl2 / 25 °C 9: 98 percent / trimethylsilyl iodide / CCl4 / 25 °C 10: 95 percent / PCC / CH2Cl2 / 25 °C 11: EtONa / ethanol / 25 °C 12: tetrahydrofuran / 25 °C 13: 96 percent / pyridine / 25 °C 14: 88 percent / EtAlCl2 / CH2Cl2 / 25 °C 15: 98 percent / hydrogen / Pd/C / ethanol / 25 °C 16: 92 percent / diisobutylaluminum hydride / CH2Cl2; toluene / -78 °C 17: 89 percent / tetrahydrofuran / 25 °C 18: 1.) Hg(OAc)2, 2.) NaBH4 / 1.) THF, H2O, 2.) 25 deg C 19: PCC / CH2Cl2 / 25 °C 20: 98 percent / tetrahydrofuran / 25 °C 21: tetrahydrofuran / 1 h / -78 °C 22: (Bu)4NF / tetrahydrofuran / 25 °C View Scheme

1: NaBH4 / ethanol 2: 96 percent / diethyl ether; tetrahydrofuran / Heating 3: pyridine / 0 °C 4: NaI / dimethylformamide; pyridine / 100 °C 5: hydrogen / Pd/C / ethanol / 25 °C 6: EtONa / ethanol / 25 °C 7: 95 percent / m-CPBA / CH2Cl2 / 25 °C 8: 98 percent / trimethylsilyl iodide / CCl4 / 25 °C 9: 95 percent / PCC / CH2Cl2 / 25 °C 10: EtONa / ethanol / 25 °C 11: tetrahydrofuran / 25 °C 12: 96 percent / pyridine / 25 °C 13: 88 percent / EtAlCl2 / CH2Cl2 / 25 °C 14: 98 percent / hydrogen / Pd/C / ethanol / 25 °C 15: 92 percent / diisobutylaluminum hydride / CH2Cl2; toluene / -78 °C 16: 89 percent / tetrahydrofuran / 25 °C 17: 1.) Hg(OAc)2, 2.) NaBH4 / 1.) THF, H2O, 2.) 25 deg C 18: PCC / CH2Cl2 / 25 °C 19: 98 percent / tetrahydrofuran / 25 °C 20: tetrahydrofuran / 1 h / -78 °C 21: (Bu)4NF / tetrahydrofuran / 25 °C View Scheme

1: 95 percent / m-CPBA / CH2Cl2 / 25 °C 2: 98 percent / trimethylsilyl iodide / CCl4 / 25 °C 3: 95 percent / PCC / CH2Cl2 / 25 °C 4: EtONa / ethanol / 25 °C 5: tetrahydrofuran / 25 °C 6: 96 percent / pyridine / 25 °C 7: 88 percent / EtAlCl2 / CH2Cl2 / 25 °C 8: 98 percent / hydrogen / Pd/C / ethanol / 25 °C 9: 92 percent / diisobutylaluminum hydride / CH2Cl2; toluene / -78 °C 10: 89 percent / tetrahydrofuran / 25 °C 11: 1.) Hg(OAc)2, 2.) NaBH4 / 1.) THF, H2O, 2.) 25 deg C 12: PCC / CH2Cl2 / 25 °C 13: 98 percent / tetrahydrofuran / 25 °C 14: tetrahydrofuran / 1 h / -78 °C 15: (Bu)4NF / tetrahydrofuran / 25 °C View Scheme