2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite in phosphate buffer; acetonitrile T=25°C; pH=6.8; 6 h;

1: With sulfonic acid type-ion exchange resin; water in toluene T=110°C; 6 h; not specified; 2: With sodium carbonate in water; toluene pH=10 - 12; 3: With hydrogenchloride; water pH=~ 1;

hydrogenchloride in water

1: With sodium hydroxide in water T=20°C; 0.5 h; 2: With hydrogenchloride in water T=0 - 5°C; pH=2 - 3; 2 h; 3: With acetic anhydride in toluene T=20°C; 12 h; Heating / reflux;

1: pyrrolidin-2-one With sodium hydride in tetrahydrofuran T=20°C; 0.75 h; 2: 2-Br-butyric acid in tetrahydrofuran T=20°C; 16 h;

1: 97 percent / hydrogen / Pd/C / methanol / 6 h / 760 Torr 2: 90 percent / 2,2,6,6-tetramethyl-1-piperidinyloxy; sodium hypochlorite; sodium chlorite / acetonitrile; aq. phosphate buffer / 6 h / 25 °C / pH 6.8 View Scheme

bis(norbornadiene)rhodium(I) tetrafluoroborate; C60H46O4P2; hydrogen in tetrahydrofuran T=20°C; P=15001.5 Torr; 18 h; Inert atmosphereAutoclave; optical yield given as percent eeenantioselective reaction;

lithium hydroxide; dihydrogen peroxide in tetrahydrofuran T=0°C; 7 h;

1.1: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 0 °C / |Inert atmosphere; |Reflux 2.1: palladium(II) oxide hydrate; hydrogen / methanol / 24 h / 20 °C / 3102.97 Torr 3.1: 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; sodium chlorite; sodium hypochlorite / acetonitrile; aq. phosphate buffer / 7 h / 35 °C / pH 6.7 3.2: 0.75 h / 20 °C / pH 8 3.3: pH 3 - 4 View Scheme

1.1: N,N'-dicyclohexylcarbodiimide / CH2Cl2 / 0.33 h / 0 °C 1.2: 24 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 16 h / -78 °C 2.1: 140 mg / LiOH*H2O; H2O2 / tetrahydrofuran / 7 h / 0 °C View Scheme