ammonium chloride; N-ethyl-N,N-diisopropylamine; HOTT reagent in N,N-dimethyl-formamide T=20°C; 0.5 h;

ammonia T=-10 - 0°C; 0.5 h;

ammonium hydroxide in acetone 2 h; Yield given;

ammonium acetate; triethylamine T=80°C; 3 h; Ionic liquid;

hydrogen bromide; acetic anhydride; acetic acid und Behandeln des Reaktionsprodukts mit Wasser;

(μ3,η2,η3,η5-acenaphthylene)Ru3(CO)7; 1,1,4,4-tetramethyldisilylethylene in ethylene glycol dimethyl ether T=80°C; 20 h; Inert atmosphere;

1: With tetrafluoroboric acid; iodobenzene; 3-chloro-benzenecarboperoxoic acid in dichloromethane; water T=25°C; Hofmann rearrangement; 48 h; Inert atmosphere; 2: With hydrogenchloride in dichloromethane; water Inert atmosphere;

1: 90 percent / (EtOPO2)4 / CHCl3 / 5 h / 80 °C 3: 1) BuLi; 2) H2O / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 1) r.t., 2 h 4: TsOH / methanol / 0.33 h / Ambient temperature 5: 96 percent / 1) 0.02N H2SO4; 2) 2N KOH / ethyl acetate; dioxane / 1) reflux, 30 min; 2) reflux, 30 min 6: diethyl ether; methanol View Scheme

1: 90 percent / (EtOPO2)4 / CHCl3 / 5 h / 80 °C 3: 1) BuLi; 2) H2O / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 1) r.t., 2 h 4: TsOH / methanol / 0.33 h / Ambient temperature 5: 96 percent / 1) 0.02N H2SO4; 2) 2N KOH / ethyl acetate; dioxane / 1) reflux, 30 min; 2) reflux, 30 min View Scheme

1: 90 percent / (EtOPO2)4 / CHCl3 / 5 h / 80 °C 3: 1) BuLi; 2) H2O / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 1) r.t., 2 h 4: TsOH / methanol / 0.33 h / Ambient temperature 5: 96 percent / 1) 0.02N H2SO4; 2) 2N KOH / ethyl acetate; dioxane / 1) reflux, 30 min; 2) reflux, 30 min 6: diethyl ether; methanol 7: 98 percent / quinoline, H2 / 5percent Pd/Lindlar / cyclohexane / 0.75 h 8: 95 percent / 2N KOH / methanol View Scheme