4-(N,N-dimethlyamino)pyridine in acetonitrile

1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 18.5 h / Inert atmosphere 2: lithium boron tetrafluoride; [Ru(2,2′-bipyridine)3][hexafluorophosphate]2; N-ethyl-N,N-diisopropylamine / hexadeuterioacetone / 1 h / 23 °C / Inert atmosphere; Irradiation View Scheme

1: sulfuryl dichloride / 2 h / 0 °C / |Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 3: manganese(IV) oxide / dichloromethane / 40 h / 20 °C 4: triethylamine; 4-(N,N-dimethlyamino)pyridine / tetrahydrofuran / 2 h / 20 °C View Scheme

1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C 2: manganese(IV) oxide / dichloromethane / 40 h / 20 °C 3: triethylamine; 4-(N,N-dimethlyamino)pyridine / tetrahydrofuran / 2 h / 20 °C View Scheme

1: manganese(IV) oxide / dichloromethane / 40 h / 20 °C 2: triethylamine; 4-(N,N-dimethlyamino)pyridine / tetrahydrofuran / 2 h / 20 °C View Scheme

TMG T=20°C; 6 h;