1: phosphorus tribromide / tetrahydrofuran / 0 °C / |Inert atmosphere 2: magnesium; dilithium tetrachlorocuprate / tetrahydrofuran / 2 h / 0 °C / |Inert atmosphere 3: o,o'-dichloro-BINOL; antimony(V) pentachloride / dichloromethane / 0.25 h / -78 °C / |Inert atmosphere 4: water; potassium permanganate; sodium periodate; sodium carbonate / tert-butyl alcohol / 12 h / 23 °C / |Inert atmosphere View Scheme

pyridine; thionyl chloride in benzene 5 h; Heating;

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere 1.2: 18 h / -78 - 20 °C / Inert atmosphere 2.1: potassium hydroxide / methanol / 13 h / 10 - 40 °C / Inert atmosphere 3.1: acetyl chloride / 8 h / 0 - 20 °C / Reflux; Inert atmosphere 4.1: copper(I) thiophene-2-carboxylate; (R)-1,1'-bis(diphenylphosphino)-2,2'-binapthyl / tetrahydrofuran / -78 °C / Inert atmosphere 5.1: sodium tetrahydroborate; water / Inert atmosphere View Scheme

lithium aluminium tetrahydride in tetrahydrofuran T=0°C; 1 h;

1: 96 percent / pyridine / diethyl ether / 0 - 20 °C 2: i-Pr2NEt; dppp / Pd(OAc)2 / dimethylsulfoxide / 12 h / 1140 Torr / Heating 3: LiAlH4 / tetrahydrofuran / 1 h / 0 °C View Scheme

1: i-Pr2NEt; dppp / Pd(OAc)2 / dimethylsulfoxide / 12 h / 1140 Torr / Heating 2: LiAlH4 / tetrahydrofuran / 1 h / 0 °C View Scheme

oxygen in octane T=40°C; P=2250.23 Torr; KineticsMechanism; Temperature;

1: 1-bromo-3-(propan-2-yl)benzene With magnesium; ethylene dibromide in tetrahydrofuran 0.5 h; Inert atmosphereReflux; 2: formaldehyd in tetrahydrofuran 1 h; Inert atmosphere;

1: With lithium aluminium tetrahydride in tetrahydrofuran T=0 - 20°C; Inert atmosphere; 2: With water in tetrahydrofuran; ethyl acetate

1.1: magnesium / tetrahydrofuran / 60 °C / Inert atmosphere 1.2: 0.67 h / Inert atmosphere 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere View Scheme