sodium periodate; sodium hydrogensulfite in water; acetonitrile

1: Pd(PPh3)4 / hexane 2: LiAlH4 / diethyl ether 3: aq. HBr; H2SO4; Bu4NHSO4 View Scheme

sodium hydride in tetrahydrofuran; oil T=75°C; Inert atmosphereCooling with ice;

chlorohydridotris(triphenylphosphine)ruthenium in benzene 1 h; Heating; Further byproducts.;

1.1: tetrahydrofuran / 20 °C 2.1: water; osmium(VIII) oxide; 4-methylmorpholine N-oxide / acetone / 20 °C 3.1: di(n-butyl)tin oxide; triethylamine / dichloromethane / 20 °C / |Inert atmosphere 4.1: pyridine / 20 °C / |Inert atmosphere 5.1: lipase PS from Burkholderia cepacia / aq. phosphate buffer / 72 h / 30 °C / |Enzymatic reaction 5.2: polymer-supported PPh3 / 1 h / 20 °C 6.1: potassium carbonate / methanol / 0 - 20 °C 7.1: copper(I) bromide / tetrahydrofuran / 1 h / -10 °C / |Inert atmosphere 8.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C / |Inert atmosphere 9.1: sodium azide / N,N-dimethyl-formamide / 16 h / 20 - 40 °C / |Inert atmosphere 10.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 20 °C / |Inert atmosphere 11.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 20 °C / |Inert atmosphere 12.1: palladium 10 on activated carbon; hydrogen / ethanol / 20 °C 13.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C / |Inert atmosphere 14.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 20 °C / |Inert atmosphere 15.1: hydrogenchloride / methanol; 1,4-dioxane / 2 h / 0 - 20 °C / |Inert atmosphere View Scheme

1: 100 percent / AlMe3 / CH2Cl2 / 10 h / Heating 2: 54.2 percent / CrO3, aq. H2SO4 / acetone / 0 - 10 °C View Scheme

1: 85 percent / Et3N / CH2Cl2 / 1 h / 0 °C 2: 1.) CuCl, 2,2'-bipyridine; 2.) HSnBu3, AIBN / 1.) ClCH2CH2Cl, 18 h, reflux; 2.) cyclohexane, 6 h, reflux View Scheme

1: 75 percent / tetrabutylammonium hydrogensulfate; aq. NaOH / 9 h / 20 °C 2: 92 percent / H2 / 5percent Pd/C(en) / tetrahydrofuran / 3 h / 20 °C View Scheme

1: thionyl chloride, N,N-dimethylaniline / benzene / 1.) at ice-bath temperature, 1 h, 2.) reflux, 1 h 2: 10 percent / benzoyl peroxide / 48 h / 80 °C / in a degassed and sealed (at 0.01 Torr) tube View Scheme

bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride in methanol; water T=100°C; Product distribution; Further Variations:Catalysts;