hydroxylamine hydrochloride in ethanol T=165°C; 20 h;

manganese(IV) oxide; trimethylsilyl trifluoromethanesulfonate; triethylamine in chloroform other Lewis acids (Et2AlCl, SnCl4, Me3SiI), other oxidants (DDQ, O2, H2O2-FeCl3, Br2); Product distribution;

magnesium; [1,3-bis(diphenylphosphino) propane] dichloronickel(II) in tetrahydrofuran; diethyl ether 20 h; Ambient temperature;

hydrogen azide; ethanol; chloroform; sulfuric acid Erhitzen einer Loesung des Reaktionsprodukts in 1-Methyl-naphthalin mit Palladium/Kohle unter Kohlendioxid;

1.1: magnesium; iodine / tetrahydrofuran / 0.5 h / |Reflux 1.2: 3 h / |Reflux 2.1: Grubb's 2nd generation catalyst / toluene / 16 h / |Inert atmosphere; |Reflux 3.1: hydrazine hydrate; potassium carbonate / 19 h / 120 - 180 °C View Scheme

1.1: tetra-n-propylammonium bromide / acetonitrile / 24 h 2.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 20 °C 2.2: 20.5 h / 20 °C / |Inert atmosphere 3.1: RuCl2(tricyclohexylphosphine)2(benzylidene) / dichloromethane / 48 h / 20 °C / |Inert atmosphere 4.1: magnesium; chloro-trimethyl-silane; ethylene dibromide / methanol / 12 h / 0 °C / |Reflux 5.1: 5 palladium on charcoal; hydrogen / ethyl acetate / 12 h / 20 °C / 760.05 Torr View Scheme

in cyclohexane T=10°C; 20 h; Irradiation;

1: 1) 0.5 M MeONa, 2) TiCl3, NaOAc / 1) MeOH, 23 deg C, 10 min 2) aq. MeOH, 4 h 2: 59.1 percent / NH2OH*HCl / ethanol / 20 h / 165 °C View Scheme

1: 88.8 percent / 10percent aq. HCl / ethanol / 20 h / Heating 2: 1) 0.5 M MeONa, 2) TiCl3, NaOAc / 1) MeOH, 23 deg C, 10 min 2) aq. MeOH, 4 h 3: 59.1 percent / NH2OH*HCl / ethanol / 20 h / 165 °C View Scheme