1: LiNH2 / dimethylsulfoxide 2: aq. HClO4 / tetrahydrofuran 3: aq. KHCO3 / 2-methyl-propan-2-ol 4: H2 / Pd-BaSO4 / pyridine View Scheme

hydrogen; palladium on barium sulfate in pyridine

1: LiNH2 / dimethylsulfoxide 2: aq. HClO4 / tetrahydrofuran 3: aq. KHCO3 / 2-methyl-propan-2-ol 4: H2 / Pd-BaSO4 / pyridine View Scheme

1: aq. KHCO3 / 2-methyl-propan-2-ol 2: H2 / Pd-BaSO4 / pyridine View Scheme

1: aq. HClO4 / tetrahydrofuran 2: aq. KHCO3 / 2-methyl-propan-2-ol 3: H2 / Pd-BaSO4 / pyridine View Scheme

hydrogen; Lindlar's catalyst in ethyl acetate

1: conc. H2SO4 / 2 h / 110 °C 2: 99 percent / WCl6, SnMe4 / benzene / 20 h / 70 °C 3: 63 percent / KH / tetrahydrofuran; pentane / 1 h / 55 °C 4: 93 percent / aq. NaOH / ethanol; tetrahydrofuran / 5 h / 80 °C View Scheme

1: 99 percent / WCl6, SnMe4 / benzene / 20 h / 70 °C 2: 63 percent / KH / tetrahydrofuran; pentane / 1 h / 55 °C 3: 93 percent / aq. NaOH / ethanol; tetrahydrofuran / 5 h / 80 °C View Scheme

1: 63 percent / KH / tetrahydrofuran; pentane / 1 h / 55 °C 2: 93 percent / aq. NaOH / ethanol; tetrahydrofuran / 5 h / 80 °C View Scheme

1.1: methanesulfonyl chloride; triethylamine / dichloromethane / 2 h / 0 - 20 °C / |Inert atmosphere 2.1: sodium iodide / acetone / 24 h / 20 °C / |Inert atmosphere 3.1: tert.-butyl lithium / diethyl ether; pentane / 1 h / -78 - 20 °C / |Inert atmosphere 3.2: 1 h / -78 - 20 °C / |Inert atmosphere 4.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 1 h / 20 °C / |Inert atmosphere 5.1: [2-(1-methylethoxy-κO)phenylmethyl-κC](nitrato-κO,κO′){rel-(2R,5R,7S)-tricyclo[3.3.1.13,7]decane-2,1-diyl[3-(2,4,6-trimethylphenyl)-1-imidazolidinyl-2-ylidene]}ruthenium / 1,2-dichloro-ethane / 8 h / 60 °C / 0.02 Torr / |Glovebox; |Inert atmosphere View Scheme