sodium methylate in N,N,N',N',N'',N''-hexamethylphosphoric triamide T=120°C;

tetra-n-butylammonium perchlorate in N,N-dimethyl-formamide T=25 - 30°C; Title compound not separated from byproducts;

1: 1,2-bis(dimethylphosphino)ethane; (indenyl)Ir(1,5-cyclooctadiene) / 16 h / 150 °C 2: aq. oxone / acetone / 0.12 h / 25 °C View Scheme

n-Pentyl nitrite T=60°C;

1: With potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); di-tert-butyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine in 1,4-dioxane; water T=100°C; 2 h; 2: With hydrogenchloride in 1,4-dioxane; water

1: 24.5 percent / Cl2 / PCl5 / 11.5 h / 195 °C 2: HF / 6 h / 140 - 160 °C / 30002.4 Torr View Scheme

1: 24.5 percent / Cl2 / PCl5 / 11.5 h / 195 °C 2: HF / 6 h / 140 - 160 °C / 30002.4 Torr 3: 89 percent Turnov. / NaNH2 / liquid ammonia / -28 deg C, 20 min; r.t., 1.5 h View Scheme

1.1: magnesium / diethyl ether 1.2: 78 percent / dichloro[1,3-bis(diphenylphosphino)propane]nickel(II) / diethyl ether / 12 h / Heating 2.1: 67 percent / boron tribromide / CH2Cl2 / 2 h / 20 °C View Scheme

1.1: lithium diisopropyl amide / tetrahydrofuran / 3.5 h / -78 - -65 °C / |Inert atmosphere; |Schlenk technique 1.2: 1 h / -75 - -65 °C / |Inert atmosphere; |Schlenk technique 2.1: iodine cloride / dichloromethane / 20 °C / |Cooling with ice 3.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 24.08 h / 80 °C / |Inert atmosphere; |Schlenk technique 4.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / water; ethylene glycol dimethyl ether / 3 h / 80 °C / |Inert atmosphere; |Schlenk technique 5.1: potassium carbonate; 2-(dicyclohexylphosphino)-2',4',6'-tri-i-propyl-1,1’-biphenyl / isopropyl alcohol / 16 h / 110 °C / |Inert atmosphere; |Sealed tube View Scheme