hydrogenchloride; palladium in ethanol

copper diacetate; air; palladium diacetate in toluene P=760 Torr; 24 h; Heating;

2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in benzene 6 h; Heating;

1: 0.887 g / LiAlH4 / tetrahydrofuran / 4 h / Heating 2: 17 percent / Cu(OAc)2; air / Pd(OAc)2 / toluene / 24 h / 760 Torr / Heating View Scheme

in diethyl ether 1.5 h; Irradiation;

1.1: NaH / dimethylformamide 1.2: NaI / acetonitrile / 24 h / Heating 2.1: 77 percent / n-Bu3SnH; AIBN / benzene / 6 h / Heating View Scheme

1: toluene / 5 h / Heating 2: 81 percent / Et3N / toluene / Heating 3: 65 percent / 1.) BuLi / tetrahydrofuran / 1.) from -78 deg C to room temp.; 2.) from -30 deg C to room temp. 4: 72 percent / diethyl ether / 1.5 h / Irradiation View Scheme

1: 81 percent / Et3N / toluene / Heating 2: 65 percent / 1.) BuLi / tetrahydrofuran / 1.) from -78 deg C to room temp.; 2.) from -30 deg C to room temp. 3: 72 percent / diethyl ether / 1.5 h / Irradiation View Scheme

1: 65 percent / 1.) BuLi / tetrahydrofuran / 1.) from -78 deg C to room temp.; 2.) from -30 deg C to room temp. 2: 72 percent / diethyl ether / 1.5 h / Irradiation View Scheme

1.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -78 °C / |Inert atmosphere 1.2: 7 h / -78 - 20 °C / |Inert atmosphere 2.1: lithium hydroxide hydrate / tetrahydrofuran; water / 17 h / 20 - 66 °C / |Inert atmosphere 2.2: 20 °C / pH 3 - 4 / |Inert atmosphere 3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C / |Inert atmosphere 4.1: tin(IV) chloride / dichloromethane / 22 h / |Reflux; |Inert atmosphere View Scheme