NH2NH2•xH2O in methanol T=20°C; 0.5 h;

1: 1-bromocyclohexane With [Fe(C2H4)4][Li(tmeda)]2 in tetrahydrofuran 2: m-bistrimethylsilylaminophenylmagnesium bromide in tetrahydrofuran; diethyl ether T=0°C; 1.5 h; Further stages.;

tetrakis(triphenylphosphine) palladium(0); sodium carbonate in ethanol; water; toluene T=100°C; Suzuki coupling; 16 h; Inert atmosphere;

1: conc. HNO3 / 100 °C 2: aq. H2SO4 / 1 h / 100 °C 3: 1.) sodium nitrite, conc. H2SO4, 2.) glacial acetic acid, CuO / 1.) 10 deg C 1 h, 2.) EtOH, 30 min 4: 59 percent / SnCl2*2H2O / ethanol / 1 h / 70 °C View Scheme

1: 1.) sodium nitrite, conc. H2SO4, 2.) glacial acetic acid, CuO / 1.) 10 deg C 1 h, 2.) EtOH, 30 min 2: 59 percent / SnCl2*2H2O / ethanol / 1 h / 70 °C View Scheme

1: aq. H2SO4 / 1 h / 100 °C 2: 1.) sodium nitrite, conc. H2SO4, 2.) glacial acetic acid, CuO / 1.) 10 deg C 1 h, 2.) EtOH, 30 min 3: 59 percent / SnCl2*2H2O / ethanol / 1 h / 70 °C View Scheme

1: acetic acid / 0.25 h 2: conc. HNO3 / 100 °C 3: aq. H2SO4 / 1 h / 100 °C 4: 1.) sodium nitrite, conc. H2SO4, 2.) glacial acetic acid, CuO / 1.) 10 deg C 1 h, 2.) EtOH, 30 min 5: 59 percent / SnCl2*2H2O / ethanol / 1 h / 70 °C View Scheme

1: p-toluidine With n-butyllithium; ZnCl2*TMEDA in tetrahydrofuran; hexane T=0 - 20°C; 0.5 h; Inert atmosphereSchlenk technique; 2: 3-[bis(trimethylsilyl)amino]phenylmagnesium chloride With N,N'-dimethyl-N,N'-propyleneurea; bis(acetylacetonate)nickel(II); 1,2-dichloro-2-methylpropane in tetrahydrofuran; hexane T=0 - 20°C; 3 h; Inert atmosphereSchlenk technique; 3: With hydrogenchloride in tetrahydrofuran; hexane; water; ethyl acetate 0.166667 h; Inert atmosphereSchlenk technique;

1: 48 percent / copper pawder / dimethylformamide / 1.5 h / Heating 2: 98 percent / tin powder, conc. HCl / ethanol / 1.5 h / Heating View Scheme

tetrakis(triphenylphosphine) palladium(0) in toluene Dimerization; 20 h; Heating;