hydrogen; palladium on activated charcoal

Oxonereg;; osmium(VIII) oxide in N,N-dimethyl-formamide T=20°C;

1.1: 91 percent Spectr. / CBr4; PPh3 / acetonitrile / Heating 2.1: disiamylborane / tetrahydrofuran / 0 °C 2.2: 62 percent / NaOH; aq. H2O2 / tetrahydrofuran / 20 °C 3.1: 75 percent / pyridinium dichromate / CH2Cl2 / 20 °C 4.1: 75 percent / 2,6-di-tert-butyl-4-methylpyridinium tetrafluoroborate / benzene / 24 h / Heating 5.1: 67 percent / Ph3SnH; AIBN / benzene-d6 / 5.5 h / 45 °C 6.1: DOWEX 50W; H2O / tetrahydrofuran / 24 h / 20 °C View Scheme

1: PPh3; DEAD / tetrahydrofuran / 0 - 20 °C 2: K2CO3 / methanol / 3 h / Heating View Scheme

1H-imidazole in dichloromethane T=20°C;

1.1: dimethyl sulfoxide; triethylamine; sulfur trioxide pyridine complex / dichloromethane / 0 °C 2.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 °C 2.2: 2 h / 20 °C View Scheme