hydrogenchloride; lithium aluminium tetrahydride; potassium ethylxanthate; nickel dichloride; sodium nitrite Yield given. Multistep reaction;

1: pyridine / dichloromethane / 24 h / 20 °C 2: C88H48F24N(1+)*Br(1-); potassium hydroxide / toluene; water / 48 h / 0 °C 3: [1,3-bis(diphenylphosphino) propane] dichloronickel(II); diisobutylaluminium hydride / toluene / 3 h / 0 - 20 °C 4: magnesium; titanium (IV) isopropoxide; chloro-trimethyl-silane / tetrahydrofuran / 20 h / 50 °C / |Inert atmosphere View Scheme

1: pyridine / dichloromethane / 24 h / 20 °C 2: C88H48F24N(1+)*Br(1-); potassium hydroxide / toluene; water / 48 h / 0 °C 3: magnesium; titanium (IV) isopropoxide; chloro-trimethyl-silane / tetrahydrofuran / 20 h / 50 °C / |Inert atmosphere 4: boron tribromide / dichloromethane / 3 h / 0 °C / |Inert atmosphere View Scheme

1: pyridine / dichloromethane / 24 h / 20 °C 2: C88H48F24N(1+)*Br(1-); potassium hydroxide / toluene; water / 48 h / 0 °C 3: [1,3-bis(diphenylphosphino) propane] dichloronickel(II); diisobutylaluminium hydride / toluene / 3 h / 0 - 20 °C 4: magnesium; titanium (IV) isopropoxide; chloro-trimethyl-silane / tetrahydrofuran / 20 h / 50 °C / |Inert atmosphere View Scheme

1: 1.) NaNO2, H2SO4, 2.) KI, H2SO4 / 1.) H2O, 0 deg C, 30 min, 2.) H2O, 4 deg C 2: 1.) Mg, 1,2-dibromoethane / 1.) THF, reflux, irradiation, 2 h, 2.) THF, benzene, RT, overnight 3: 30percent H2O2, AcOH / 2 h / 70 °C View Scheme

hydrogenchloride; hypophosphorous acid; sodium nitrite 1.) water, 20 min, 0 deg C, 2.) 45 min, 4 deg C; Multistep reaction;