tetrabutyl ammonium fluoride in tetrahydrofuran 5.5 h; Heating;

1: 67 percent / 9-acetylanthracene / tetradeuteriomethanol / 1.5 h / Irradiation 2: 1.) SO2, 2.) NaHCO3 / 1.) CH2Cl2, -15 deg C, 2.5 h, 2.) EtOH, 78 deg C, 2.5 h View Scheme

sulfur dioxide; sodium hydrogencarbonate 1.) CH2Cl2, -15 deg C, 2.5 h, 2.) EtOH, 78 deg C, 2.5 h; Yield given. Multistep reaction;

1: 1.) O3, 2.) NaBH4 / 1.) CH2Cl2, MeOH, -10 deg C, 45 min, 2.) room temperature, 2 h 2: 47 percent / NaHCO3 / aq. ethanol / 5 h / Heating 3: 87 percent / imidazole, PPh3, I2 / CH2Cl2 / 1.5 h / Ambient temperature 4: 77 percent / Zn, NiCl2*6H2O, I2 / pyridine / 0.75 h / Ambient temperature 5: 82 percent / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) room temperature, 3 h 6: 81 percent / n-Bu4NF / tetrahydrofuran / 5.5 h / Heating View Scheme

1: 87 percent / imidazole, PPh3, I2 / CH2Cl2 / 1.5 h / Ambient temperature 2: 77 percent / Zn, NiCl2*6H2O, I2 / pyridine / 0.75 h / Ambient temperature 3: 82 percent / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) room temperature, 3 h 4: 81 percent / n-Bu4NF / tetrahydrofuran / 5.5 h / Heating View Scheme

1: 77 percent / Zn, NiCl2*6H2O, I2 / pyridine / 0.75 h / Ambient temperature 2: 82 percent / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) room temperature, 3 h 3: 81 percent / n-Bu4NF / tetrahydrofuran / 5.5 h / Heating View Scheme

1: 82 percent / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) room temperature, 3 h 2: 81 percent / n-Bu4NF / tetrahydrofuran / 5.5 h / Heating View Scheme

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