triethylamine in dichloromethane 0.0833333 h;

sodium acetate in acetic acid 0.0333333 h; Heating;

(i) Pb(OAc)4, AcOH, (ii) Et3N; Multistep reaction;

1: 35 percent / sodium dithionite / methanol; H2O / 5 h 2: 87 percent / lead(IV) acetate / acetic acid / 2 h 3: 90 percent / Et3N / CH2Cl2 / 0.08 h View Scheme

1: CH2Cl2 / Ambient temperature 2: CH2Cl2 / Ambient temperature 3: 95 percent / benzene / 24 h / Heating 4: 35 percent / sodium dithionite / methanol; H2O / 5 h 5: 87 percent / lead(IV) acetate / acetic acid / 2 h 6: 90 percent / Et3N / CH2Cl2 / 0.08 h View Scheme

1: 50 percent / lead(IV) acetate / acetic acid / 0.25 h 2: CH2Cl2 / Ambient temperature 3: CH2Cl2 / Ambient temperature 4: 95 percent / benzene / 24 h / Heating 5: 35 percent / sodium dithionite / methanol; H2O / 5 h 6: 87 percent / lead(IV) acetate / acetic acid / 2 h 7: 90 percent / Et3N / CH2Cl2 / 0.08 h View Scheme

1: 95 percent / benzene / 24 h / Heating 2: 35 percent / sodium dithionite / methanol; H2O / 5 h 3: 87 percent / lead(IV) acetate / acetic acid / 2 h 4: 90 percent / Et3N / CH2Cl2 / 0.08 h View Scheme

potassium acetate 1.) glacial acetic acid, toluene, -10 deg C, 4 d, 2.) reflux, 5 min; Yield given. Multistep reaction;

sulfuric acid T=0°C; 0.25 h;

1: 99 percent / trifluoromethanesulfonic acid / 0.01 h / ice-bath 2: 95 percent / pyridine / 24 h / 50 °C 3: 1.) ozone in oxygen, 2.) dimethyl sulfide, pyridine / 1.) CH2Cl2, CH3OH, -70 deg C, 2.) 25 deg C, 18 h 4: 10 percent / p-toluenesulfonic acid / benzene / 3 h / Heating View Scheme