1: 95 percent / (Ph3P)3RhCl / CH2Cl2 / 18 h / Ambient temperature 2: 75 percent / diisobutylaluminum hydride / diethyl ether; toluene / 2 h / -10 °C View Scheme

hydrogenchloride in acetone 4 h; Ambient temperature;

in diethyl ether 0.0333333 h;

1: 1.) O3, 2.) acetic anhydride, sodium acetate, 3.) H2O; / 1.) cyclohexane, glacial acetic acid, 2.) glacial acetic acid, 3.) boiling; 2: 85 percent / diethyl ether / 0.03 h View Scheme

1: 90 percent / p-toluenesulfonic acid / 10 h / Ambient temperature 2: 99 percent / 5percent aq. hydrochloric acid / acetone / 4 h / Ambient temperature View Scheme

acetic anhydride; sodium hydrogencarbonate; ozone; triethylamine 1) CH2Cl2, -40 deg C, 8 h, 2a) CH2Cl2, -20 deg C, 2b) 25 deg C, overnight; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

acetic anhydride; sodium hydrogencarbonate; ozone; triethylamine 1.) CH2Cl2; Yield given. Multistep reaction;

1: 95 percent / (Ph3P)3RhCl / CH2Cl2 / 18 h / Ambient temperature 2: 75 percent / diisobutylaluminum hydride / diethyl ether; toluene / 2 h / -10 °C 3: 85 percent / triphenylphosphine, bromine / CCl4 / 15 °C 4: 1) cuprous iodide, 2,2'-bipyridyl; 2) magnesium / 1) abs. THF, 2 deg C, 10 min; 2) abs. THF. 5: 1) water, p-toluenesulfonic acid; 2) pyridine / 1) methanol, room temp., 2) room temp. View Scheme

Wilkinson's catalyst in dichloromethane 18 h; Ambient temperature; Yield given;

1: 18.8 g / pyridine / diethyl ether / 3 h / Ambient temperature 2: 1.) NaH, dimethylsulfoxide / 1.) 20 min, 20 deg C, 2.) benzene, 30 min 3: diethyl ether View Scheme