1: 34 percent / TiCl4 / CH2Cl2 / 1 h / 0 °C 2: 76 percent / N-bromosuccinimide, benzoyl peroxide / CCl4 / Heating 3: 80 percent / K2CO3, LiI / 18-crown-6 / acetone / 16 h / Heating View Scheme

1.1: n-butyllithium / hexane; tetrahydrofuran / 0.25 h / -78 °C 1.2: 0.75 h / -78 - 0 °C 2.1: sodium hexamethyldisilazane / tetrahydrofuran / -78 °C 2.2: 6 h / -50 °C 3.1: lithium borohydride / tetrahydrofuran / 0 °C 4.1: 1H-imidazole / dichloromethane / 20 °C 5.1: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -40 °C 6.1: triphenylphosphine; carbon tetrabromide / dichloromethane / 0.5 h / 20 °C / |Inert atmosphere 7.1: N,N,N',N,-tetramethylethylenediamine; anhydrous iron chloride / tetrahydrofuran / 0.5 h / 0 °C 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C 9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C 10.1: tetrahydrofuran / 2.25 h / 0 - 20 °C 11.1: pyridine / 20 °C 12.1: potassium tert-butylate / dimethyl sulfoxide / 5 h / 20 °C 13.1: methyl-magnesium iodide / diethyl ether / 0.17 h / 180 °C / |Inert atmosphere View Scheme

1.1: n-butyllithium / hexane; tetrahydrofuran / 0.25 h / -78 °C 1.2: 0.75 h / -78 - 0 °C 2.1: sodium hexamethyldisilazane / tetrahydrofuran / -78 °C 2.2: 6 h / -50 °C 3.1: lithium borohydride / tetrahydrofuran / 0 °C 4.1: 1H-imidazole / dichloromethane / 20 °C 5.1: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -40 °C 6.1: triphenylphosphine; carbon tetrabromide / dichloromethane / 0.5 h / 20 °C / |Inert atmosphere 7.1: N,N,N',N,-tetramethylethylenediamine; anhydrous iron chloride / tetrahydrofuran / 0.5 h / 0 °C 8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C 9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 °C 10.1: tetrahydrofuran / 2.25 h / 0 - 20 °C 11.1: pyridine / 20 °C 12.1: potassium tert-butylate / dimethyl sulfoxide / 5 h / 20 °C 13.1: methyl-magnesium iodide / diethyl ether / 0.17 h / 180 °C / |Inert atmosphere View Scheme

pyridine; benzene d-citronellyl tigliate;

in water Yield given;

toluene

2: MCPBA / CH2Cl2 / 12 h / 35 °C 3: 76 percent / LiAlH4 / tetrahydrofuran / 4 h / Heating View Scheme

1: 84 percent / AlCl3 / Heating 2: 82 percent / LiAlH4 / diethyl ether / Heating 3: 83 percent / p-toluenesulfonic acid / toluene / 5 h / Heating View Scheme

phenyllithium in 1,4-dioxane; diethyl ether; benzene 0.0833333 h;

1: 78 percent / 1.88 M phenyllithium / diethyl ether; benzene; dioxane / 0.08 h 2: 26 percent / ceric ammonium nitrate (CAN), pyridine-2,6-dicarboxylic acid N-oxide / acetonitrile; H2O / 0.25 h View Scheme