ruthenium trichloride; sodium tetrahydroborate in N,N-dimethyl acetamide; water T=0°C; 1 h;

1: 82 percent / triethylamine / CH2Cl2 / 0 - 20 °C 2: 78 percent / bis(tricyclohexylphosphine) benzylidene Ru(IV) dichloride / CH2Cl2 / 6 h / Heating View Scheme

1.1: 1H-imidazole / dichloromethane / 2 h / 0 °C / Inert atmosphere 2.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; toluene / 20 °C 3.1: sodium periodate / tetrahydrofuran; water / 1 h 4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 4.2: 4 h / -78 - 20 °C 5.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 6.1: hydrogen; palladium(II) oxide hydrate / benzene / 5 h / 20 °C 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 0 °C / Inert atmosphere View Scheme

1: carbon monoxide With triphenylphosphine; palladium dichloride in toluene T=80°C; P=7500.75 Torr; 2 h; 2: 4-hydroxy-1-nonene With tin(ll) chloride in water; toluene T=80 - 100°C; 18 h; Product distribution / selectivity;

1: carbon monoxide With triphenylphosphine; palladium dichloride in toluene T=80°C; P=7500.75 Torr; 2 h; 2: 4-hydroxy-1-nonene With tin(ll) chloride in water; toluene T=80 - 100°C; 18 h; Product distribution / selectivity;

1: carbon monoxide With triphenylphosphine; palladium dichloride in toluene T=80°C; P=7500.75 Torr; 2: 4-hydroxy-1-nonene With tin(ll) chloride in water; toluene T=80°C; P=3000.3 - 15001.5 Torr; 11.5 h; Product distribution / selectivity;

pyridine

1: triethylamine / 20 °C / |Cooling with ice; |Inert atmosphere 2: Grubb's 2nd generation catalyst / toluene / 1.5 h / |Reflux; |Inert atmosphere 3: N-bromosuccinmide; 2,2'-azo-bisisobutyronitrile / chlorobenzene / 8 h / 120 °C / |Inert atmosphere 4: triethylamine / 96 h / |Reflux; |Inert atmosphere View Scheme