1: With sulfuric acid; sodium nitrite in water T=0°C; 0.333333 h; 2: in water T=120°C; 1 h;

sodium nitrite in water; Petroleum ether

[Ru2(p-PriC6H4Me)2(μ-Cl)Cl]2; 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate); trifluoroacetic acid; trifluoroacetic anhydride T=105°C; 10.5 h;

1.1: NaH / dimethylformamide / 0.5 h / 20 °C 1.2: 80 percent / dimethylformamide / 48 h / 20 °C 2.1: H2SO4; NaNO2 / H2O / 0.33 h / 0 °C 2.2: 77 percent / H2O / 1 h / 120 °C View Scheme

T=240°C; 0.333333 h; Yield given;

1: 95 percent / 25percent aq. TiCl3, AcOH / 0.15 h / Ambient temperature 2: 1.) aq. NaNO2, H2SO4 / 2.) 120 deg C, 1 h View Scheme

1: 81 percent / K2CO3 / acetone / 3.5 h / Heating 2: 98 percent / 10percent aq. KOH / 3 h / Heating View Scheme

1.1: 88 percent / 1,5,7-triazabicyclo[4.4.0]dec-5-ene / acetonitrile / 20 h / 20 °C 2.1: 71 percent / 1 h / 230 °C 3.1: O3 / methanol / 0.5 h / -78 °C 3.2: dimethyl sulfide / methanol / -78 - 20 °C 4.1: 5.9 g / H3PO4 / H2O / 0.33 h / 100 °C 5.1: 90 percent / KOH / methanol; H2O / 1 h / Heating View Scheme

1.1: 88 percent / 1,5,7-triazabicyclo[4.4.0]dec-5-ene / acetonitrile / 20 h / 20 °C 2.1: 71 percent / 1 h / 230 °C 3.1: O3 / methanol / 0.5 h / -78 °C 3.2: dimethyl sulfide / methanol / -78 - 20 °C 4.1: 5.9 g / H3PO4 / H2O / 0.33 h / 100 °C View Scheme

1.1: 88 percent / 1,5,7-triazabicyclo[4.4.0]dec-5-ene / acetonitrile / 20 h / 20 °C 2.1: 71 percent / 1 h / 230 °C 3.1: O3 / methanol / 0.5 h / -78 °C 3.2: dimethyl sulfide / methanol / -78 - 20 °C 4.1: 5.9 g / H3PO4 / H2O / 0.33 h / 100 °C 5.1: 90 percent / KOH / methanol; H2O / 1 h / Heating 6.1: DPPA; Et3N; t-BuOH / 18 h / Heating 6.2: TFA / CH2Cl2 / 1 h / 0 °C View Scheme