diisopropylamine in N,N-dimethyl-formamide T=80°C; 17 h; Inert atmosphere;

hydrogen fluoride; K-oxalate; potassium carbonate; 4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane in dimethyl sulfoxide Heating;

1: 1) HBF4, NaNO2, 2) Cu, NaNO2 / 1) H2O, 30 min, 2) H2O, 1 h 2: 75 percent / conc. HCl / methanol / 0.5 h / 120 °C 3: 21 percent / KI / toluene; dimethylsulfoxide / 100 - 110 °C 4: 45 percent / HF, potassium carbonate, potassium oxalate, kryptofix 222 / dimethylsulfoxide / Heating View Scheme

1: 90 percent / 4 M NaOH / ethanol / 2 h / Heating 2: 1) HBF4, NaNO2, 2) Cu, NaNO2 / 1) H2O, 30 min, 2) H2O, 1 h 3: 75 percent / conc. HCl / methanol / 0.5 h / 120 °C 4: 21 percent / KI / toluene; dimethylsulfoxide / 100 - 110 °C 5: 45 percent / HF, potassium carbonate, potassium oxalate, kryptofix 222 / dimethylsulfoxide / Heating View Scheme

1: 20 percent / AlCl3 / CS2 / room temperature, 30 min; 60 deg C, 2 h 2: 90 percent / 4 M NaOH / ethanol / 2 h / Heating 3: 1) HBF4, NaNO2, 2) Cu, NaNO2 / 1) H2O, 30 min, 2) H2O, 1 h 4: 75 percent / conc. HCl / methanol / 0.5 h / 120 °C 5: 21 percent / KI / toluene; dimethylsulfoxide / 100 - 110 °C 6: 45 percent / HF, potassium carbonate, potassium oxalate, kryptofix 222 / dimethylsulfoxide / Heating View Scheme

1: 75 percent / conc. HCl / methanol / 0.5 h / 120 °C 2: 21 percent / KI / toluene; dimethylsulfoxide / 100 - 110 °C 3: 45 percent / HF, potassium carbonate, potassium oxalate, kryptofix 222 / dimethylsulfoxide / Heating View Scheme

1: 21 percent / KI / toluene; dimethylsulfoxide / 100 - 110 °C 2: 45 percent / HF, potassium carbonate, potassium oxalate, kryptofix 222 / dimethylsulfoxide / Heating View Scheme

tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide 1.) o-dichlorobenzene, 25 deg C, 2 min, 2.) 110 deg C, 30 min; Yield given. Multistep reaction. Yields of byproduct given;

tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide 1.) o-dichlorobenzene, 25 deg C, 2 min, 2.) 110 deg C, 30 min; Yield given. Multistep reaction. Yields of byproduct given;

sodium hydride in N,N-dimethyl-formamide