1: piperidin-2-one With sodium hydride in tetrahydrofuran 2: allyl bromide in tetrahydrofuran

tetrabutyl ammonium fluoride in tetrahydrofuran; dimethyl sulfoxide T=80°C; 1.5 h;

[Cu(μ-OH)(tmeda)]2Cl2; caesium carbonate in acetonitrile T=20°C; 6 h;

1: 64 percent / dicyclohexylcarbodiimide; 4-(N,N-dimethylamino)pyridine / dimethylformamide / 18 h / 30 °C 2: 80 percent / [1,3-dimesitylimidazolidin-2-yl]Cl2(PCy3)Ru=CHPh / CH2Cl2 / 18 h / 20 °C 3: 98 percent / H2 / PtO2 / benzene / 18 h / 20 °C / 760.05 Torr 4: 99 percent / Bu4NF / tetrahydrofuran; dimethylsulfoxide / 1.5 h / 80 °C View Scheme

1: 80 percent / [1,3-dimesitylimidazolidin-2-yl]Cl2(PCy3)Ru=CHPh / CH2Cl2 / 18 h / 20 °C 2: 98 percent / H2 / PtO2 / benzene / 18 h / 20 °C / 760.05 Torr 3: 99 percent / Bu4NF / tetrahydrofuran; dimethylsulfoxide / 1.5 h / 80 °C View Scheme

1: 100 mg / aq. NaHCO3; Na2CO3 / acetone 2: 92 percent / NaH / tetrahydrofuran / 20 °C View Scheme

1: NaIO4; aq. RuCl3 / 1,2-dichloro-ethane / 20 °C 2: 100 mg / aq. NaHCO3; Na2CO3 / acetone 3: 92 percent / NaH / tetrahydrofuran / 20 °C View Scheme

T=120°C;

potassium meta-periodate; [Ru(η3:η2:η3-C12H18)Cl2] in water T=100°C; 0.3 h;