1: 1.) Mg / 1.) THF, room t., 2.) THF, room t., 1 h 2: p-TsOH / benzene / 16 h / Heating 3: 1.) O3, 2.) Me2S / 1.) CH2Cl2, -78 deg C, 10 min, 2.) -78 deg C to room t. 4: Jones reagent / acetone / 0.5 h / 0 °C 5: 87.2 percent / 95 percent H2SO4 / 5 h / Heating 6: 75 percent / diethyl ether; toluene / 0.5 h / -78 °C 7: 81.5 percent / ZnI2 / 1,2-dichloro-ethane / 0.17 h / Ambient temperature 8: 1.) BuLi(hexane), (i-Pr)2NH / 1.) THF, -78 deg C, 1 h 2.) THF, -78 deg C, 1 h, to room t. 9: 100 percent / p-MeC6H4SO2N3, Et3N / CH2Cl2 / 4 h / Ambient temperature 10: multistep reaction; reactions under var. conditions <Rh(OAc)2, Cu(acac)2, R-1648 catalist> 11: 90 percent / NaBH4, NiCl2*6H2O / methanol / 24 h / Ambient temperature 12: 1.) BuLi(hexane), (i-Pr)NH / 1.) HMPA, THF, 0 deg C, 2 h, 2.) HMPA, THF, 0 deg C to room t., 2 h 13: 91.2 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 14: 92.3 percent / PCC / CH2Cl2 / 3 h / Ambient temperature 15: 1.) 80 percent N2H4*H2O, 2.) Na / 1.) diethylene glycol, ethyleneglycol, 184 deg C, 1.5 h, 2.) diethylene glycol, ethyleneglycol, 70 deg C, then 4 h, reflux View Scheme

tetrakis(triphenylphosphine) palladium(0); tetrabutyl ammonium fluoride; silver(l) oxide in tetrahydrofuran; N,N-dimethyl-formamide T=90°C; 18 h;

n-butyllithium; Zinc chloride; tetrakis (triphenylphosphine) palladium (0) in tetrahydrofuran; hexane; chloroform; water

pyridine; triphenylphosphine; nickel dichloride

NiCl2((PPh3)P)2; n-butyllithium; methylmagnesium bromide; zinc(II) chloride Yield given. Multistep reaction;

1.1: magnesium / tetrahydrofuran / 1 h / |Inert atmosphere; |Schlenk technique; |Reflux 1.2: 4.33 h / -95 - 20 °C / |Inert atmosphere; |Schlenk technique 2.1: sulfuric acid / tetrahydrofuran; diethyl ether; water / 0.17 h / 20 °C / |Inert atmosphere; |Schlenk technique 3.1: tetrahydrofuran; diethyl ether / 20 h / 60 °C / |Inert atmosphere; |Schlenk technique 4.1: 2,2'-azo-bisisobutyronitrile; N-bromosuccinmide / tetrachloromethane / 3 h / |Inert atmosphere; |Schlenk technique; |Reflux; |Irradiation View Scheme

1: With magnesium in tetrahydrofuran Heating; 2: With boric acid trimethyl ester in tetrahydrofuran; diethyl ether T=20°C; 2 h; 3: With hydrogenchloride in tetrahydrofuran; diethyl ether 1 h;

Mg; I2 in tetrahydrofuran

1: para-bromotoluene With n-butyllithium in tetrahydrofuran; hexane T=-78 - -10°C; 2: tri-isopropoxy-borane in tetrahydrofuran; hexane T=-78 - 20°C;

hydrogenchloride; water in tetrahydrofuran (Ar); stirring (-30°C), stirring (room temp., overnight), hydrolysis (0°C, water, 4M HCl), evapn. of the solvent, extn. (ether); evapn. of the solvent, recrystn. (water); elem. anal.;