[RhCl(η2:η2-cycloocta-1,5-diene)]2; potassium carbonate; tris-(dimethylamino)-phosphine; caesium carbonate in toluene T=100°C; 20 h;

[RhCl(η2:η2-cycloocta-1,5-diene)]2; potassium carbonate; caesium carbonate; tris-(dimethylamino)-phosphine in toluene T=100°C; 20 h; Inert atmosphere;

1.1: n-BuLI / tetrahydrofuran / 0.5 h / 0 °C 1.2: tetrahydrofuran / 4 h / 20 °C 2.1: Bu4NF / tetrahydrofuran / 8 h / 26 °C 3.1: m-chloroperbenzoic acid / CH2Cl2 / 3 h / 28 °C 4.1: 95 percent / [tris(1-pyrazolyl)borate]RuPPh3(CH3CN)2PF6 / toluene / 3 h / 100 °C View Scheme

1: m-chloroperbenzoic acid / CH2Cl2 / 3 h / 28 °C 2: 95 percent / [tris(1-pyrazolyl)borate]RuPPh3(CH3CN)2PF6 / toluene / 3 h / 100 °C View Scheme

1: Bu4NF / tetrahydrofuran / 8 h / 26 °C 2: m-chloroperbenzoic acid / CH2Cl2 / 3 h / 28 °C 3: 95 percent / [tris(1-pyrazolyl)borate]RuPPh3(CH3CN)2PF6 / toluene / 3 h / 100 °C View Scheme

1.1: 100 percent / H2 / Pd/C / ethyl acetate / 1.25 h / 20 °C / 760 Torr 2.1: NaBH4 / methanol / 1.5 h / 20 °C 3.1: 4.13 g / H2SO4 / 0.5 h / Heating 4.1: O3 / CH2Cl2 / -78 °C 4.2: 71 percent / dimethyl sulfide / CH2Cl2 / 29.5 h / -78 - 20 °C 5.1: 100 percent / NaOH / H2O / 2 h / 20 °C View Scheme

1.1: 95 percent / sodium methoxide / methanol / 13 h / 20 °C 2.1: 100 percent / H2 / Pd/C / ethyl acetate / 1.25 h / 20 °C / 760 Torr 3.1: NaBH4 / methanol / 1.5 h / 20 °C 4.1: 4.13 g / H2SO4 / 0.5 h / Heating 5.1: O3 / CH2Cl2 / -78 °C 5.2: 71 percent / dimethyl sulfide / CH2Cl2 / 29.5 h / -78 - 20 °C 6.1: 100 percent / NaOH / H2O / 2 h / 20 °C View Scheme

1.1: O3 / CH2Cl2 / -78 °C 1.2: 71 percent / dimethyl sulfide / CH2Cl2 / 29.5 h / -78 - 20 °C 2.1: 100 percent / NaOH / H2O / 2 h / 20 °C View Scheme

methylamine in water sealed tube;

1: N-bromosuccinmide; dibenzoyl peroxide / 1,2-dichloro-ethane / 10 h / |Reflux; |Inert atmosphere 2: palladium 10 on activated carbon; hydrogen / ethyl acetate; dichloromethane / 10 h / 20 °C / |Inert atmosphere 3: boron trifluoride diethyl etherate; tert.-butylnitrite / dichloromethane / 1 h / 0 - 20 °C / |Inert atmosphere 4: water / tetrahydrofuran / 1 h / 60 °C / |Inert atmosphere View Scheme