water; oxygen; rose bengal in acetone T=0°C; 7 h; Irradiation;

1: 79 percent / 3-chloroperbenzoic acid / CH2Cl2 / 3 h / Ambient temperature 2: 90 percent / Ag2O / acetone / 24 h / Ambient temperature 3: 95 percent / hydrogen / Pd-C / ethanol / 0.5 h / 825.07 Torr / Ambient temperature 4: 1.) 85 percent aq. hydrazine, 2.) KOH / 1.) ethylene glycol, 100 deg C, 3 h, 2.) 100 deg C, 24 h 5: 94 percent / Jones reagent / acetone / 0.5 h / 0 °C View Scheme

1: 79 percent / 3-chloroperbenzoic acid / CH2Cl2 / 3 h / Ambient temperature 2: 83 percent / triethylamine / CH2Cl2 / 2 h / Ambient temperature 3: 59 percent / hydrogen / 10 percent Pd-C / ethyl acetate / 3 h / 750.06 Torr / Ambient temperature 4: 98 percent / LiAlH4 / diethyl ether / 1.67 h / Ambient temperature View Scheme