bis(η4-1,5-cyclooctadiene)-di-μ-methoxy-diiridium(I) in octane T=100°C; 24 h; Inert atmosphereSealed tube;

1: 1.) n-BuLi / 1.) THF, hexane, a) 0 deg C, 1 h, b) RT, 15 min, 2.) THF, hexane, a) from -78 deg C to RT, b) RT, 12 h 2: 31 percent / aq. HCl / tetrahydrofuran / 6 h / 60 °C View Scheme

1.1: N,N,N',N'-tetramethylethylenediamine; n-BuLi / hexane; diethyl ether / 1 h / 0 °C 1.2: hexane; diethyl ether / 0.5 h / 0 °C 2.1: N,N,N',N'-tetramethylethylenediamine; n-BuLi / hexane; diethyl ether / 1 h / 0 °C 2.2: 1.1 g / hexane; diethyl ether / 0.25 h / -78 °C 3.1: aq. HCl / tetrahydrofuran / 20 °C View Scheme

n-butyllithium 1.) ether, hexane, 2 h, r.t., 2.) 30 min, r.t.; Yield given. Multistep reaction;

n-butyllithium 1.) ether, hexane, 2 h, r.t., 2.) 5 min, r.t.; Yield given. Multistep reaction;

1.1: n-BuLi; TMEDA / hexane / 1.5 h / 20 °C 1.2: 61 percent / hexane / 16 h / 20 °C 2.1: 77 percent / HCl / methanol / 1 h / 20 °C View Scheme

1: (methoxymethyleneoxy)phenol With n-butyllithium; N,N,N',N,-tetramethylethylenediamine in hexane T=20°C; 1.5 h; 2: chloro-diphenylphosphine in hexane T=20°C; 16 h;

n-butyllithium 1.) ether, hexane, 2 h, r.t., 2.) 30 min, r.t.; Yield given. Multistep reaction;

1.1: n-butyllithium; N,N,N',N,-tetramethylethylenediamine / hexane / 1.25 h / Inert atmosphere; Cooling with ice 1.2: 1 h / 20 °C / Cooling with ice 2.1: n-butyllithium; N,N,N',N,-tetramethylethylenediamine / hexane / 1.25 h / Inert atmosphere; Cooling with ice 2.2: 1 h / 20 °C / Cooling with ice 3.1: hydrogenchloride; water / methanol / 4 h / 90 °C 4.1: bromine; acetic acid / 0.33 h / 20 °C / Cooling with ice 5.1: N,N-dimethyl-formamide / 5 h / 154 °C 6.1: sodium hydride / 1,4-dioxane / 0.03 h / 20 °C 6.2: 0.17 h / 20 °C 6.3: 6 h / 155 °C 7.1: ammonia / 1,4-dioxane / 24 h / 150 °C View Scheme