bis (triortho-tolylphosphine)palladium(II) chloride; tri-n-butyltin methoxide in dimethyl sulfoxide T=100°C; 14 h; Inert atmosphere; regioselective reaction;

hydrogenchloride in diethyl ether

1: (i) dioxane, (ii) H2O, Et2O 2: aq. HCl / diethyl ether View Scheme

oxygen; nitrogen(IV) oxide; ozone in dichloromethane T=-10°C; 5 h; Yield given. Yields of byproduct given;

1: hydroxylamine hydrochloride, pyridine / methanol / 0.5 h / Heating 2: trifluoroperacetic acid, Na2HPO4, urea / acetonitrile / 1.25 h / Heating View Scheme

1: 90 percent / SnCl2*2H2O / ethyl acetate / Heating 2: 1) NaNO2, HCl, 2) 10percent NaOH / 2) EtOH 3: 1) t-BuOK / 1) DMSO, 2) DMSO, irradiation 4: 98 percent / hydrogen, HClO4 / 10percent Pd/C / ethanol / 6 h / 25 °C / 3000.2 Torr 5: 83 percent / t-BuOK / tetrahydrofuran / 0.5 h / 25 °C 6: 88 percent / 10N KOH / tetrahydrofuran / 24 h / 25 °C View Scheme

copper(l) iodide; 1,10-phenanthroline in o-xylene T=150°C; 6 h; Inert atmosphere;

hydrogenchloride; tin in ethanol