1: 70 percent / toluene-p-sulphonic acid / toluene / 24 h / Heating 2: 2.) 30percent sodium hydroxide / 1.) toluene, reflux, 2 d; 2.) water, reflux, 2 h 3: 41 percent / butyl-lithium / tetrahydrofuran / 1.) -78 degC, 4 h, 2.) -78 degC to R. T. 4: 85 percent / m-chloroperbenzoic acid / CHCl3 / 2 h / Ambient temperature 5: 95 percent / toluene / 6 h / 100 °C 6: 75 percent / 1.) butyl-lithium, 2.) benzaldehyde, H2O / tetrahydrofuran / 1.) -60 degC, 2.) -78 degC to R. T. View Scheme

((Me)N2N)Ni-Cl in tetrahydrofuran; isobutyramide T=-35 - 20°C; Inert atmosphere;

piperidine; n-butyllithium; (Brommethyl)triphenylphosphoniumbromid in diethyl ether; hexane 12 h; Heating;

piperidine; n-butyllithium 1.) ether, hexane, 20 deg C, 2 h, 2.) ether, hexane, reflux, 12 h; Yield given. Multistep reaction. Yields of byproduct given;

1: 70 percent / toluene-p-sulphonic acid / toluene / 24 h / Heating 2: 2.) 30percent sodium hydroxide / 1.) toluene, reflux, 2 d; 2.) water, reflux, 2 h 3: 18 percent / 50percent sodium hydride / dimethylformamide / 1 h / 50 °C View Scheme

sodium iodide in acetone Reflux;

diiodo monosilane in dichloromethane T=-42°C; 0.0833333 h;

triethyl borane in hexane; benzene T=25°C; 0.0833333 h;

anhydrous iron chloride; water; AgNTf2 in 1,4-dioxane T=95°C; 60 h; regioselective reaction;

hydrogen iodide in water