tert.-butylnitrite; boron trifluoride diethyl etherate in 1,2-dichloro-benzene T=105°C; Balz-Schiemann Reaction; 0.75 h;

1: With isopropylmagnesium chloride lithium chloride complex in tetrahydrofuran T=0°C; Inert atmosphere; 2: With N-fluoro-N-(phenylsulfonyl)benzene-sulfonamide in dichloromethane; perfluorodecahydronaphthalene T=-78 - 25°C; Inert atmosphere;

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C 1.2: 0.5 h 2.1: Cu(OTf)2; potassium fluoride; 18-crown-6 ether / N,N-dimethyl-formamide / 18 h / 60 °C View Scheme

1: 3.6 g / TFA; aq. H2O2 / 20 h / 70 - 75 °C 2: 59 percent / conc. H2SO4; KNO3 / 2 h / 120 °C 3: 91 percent / H2 / Raney Ni / ethanol / 3 h / 2068.59 Torr 4: 83 percent / conc. H2SO4; KNO3 / 0 - 20 °C 5: 90 percent / conc. H2SO4 / 20 °C 6: 94 percent / H2 / Raney Ni / ethanol View Scheme

1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); zinc

1: 3.6 g / TFA; aq. H2O2 / 20 h / 70 - 75 °C 2: 59 percent / conc. H2SO4; KNO3 / 2 h / 120 °C 3: 91 percent / H2 / Raney Ni / ethanol / 3 h / 2068.59 Torr 4: 83 percent / conc. H2SO4; KNO3 / 0 - 20 °C 5: 90 percent / conc. H2SO4 / 20 °C View Scheme

1: 3.6 g / TFA; aq. H2O2 / 20 h / 70 - 75 °C 2: 59 percent / conc. H2SO4; KNO3 / 2 h / 120 °C 3: 91 percent / H2 / Raney Ni / ethanol / 3 h / 2068.59 Torr View Scheme

ammonium hydroxide T=180°C; 52 h; Yield given. Yields of byproduct given;

1.1: trifluoroacetic acid; dihydrogen peroxide / water / 70 - 75 °C 2.1: potassium nitrate; sulfuric acid / 2 h / 120 °C 2.2: 15 °C / Cooling with ice 3.1: hydrogen / Raney nickel / ethanol / 3 h / 2068.65 Torr 4.1: potassium nitrate; sulfuric acid / 1.17 h / 0 - 20 °C 4.2: 12 h / 20 °C 4.3: 5 °C / Cooling with ice 5.1: hydrogen / Raney nickel / ethanol / 2 h / 1861.78 Torr 6.1: oxygen; anhydrous iron chloride / 1,4-dioxane; ethanol / 10 h / 75 °C 6.2: Cooling with ice 7.1: trimethylsilyl bromide / anhydrous propionitrile / 12 h / 120 °C 7.2: 23 °C / Cooling with ice View Scheme

hydrazine hydrate in propan-1-ol; sodium hydrogencarbonate