pyridine 0.5 h; Heating;

T=90 - 95°C;

12 h; Heating;

1: 63 percent / Pb(OAc)4, Cu(OAc)2, pyridine / benzene / 4 h / Heating 2: 90 percent / Li/ethylenediamine / 0.25 h / Heating 3: pyridine / 18 h / Ambient temperature 4: 1.) O3, 2.) Jones reagent / 1.) CH2Cl2, -10 deg C, 2.) acetone, 0 deg C 5: 73 percent 6: 72 percent / H2SO4 / ethanol / 24 h / Heating View Scheme

1: 4-dimethylaminopyridine, proton sponge / 1,2-dichloro-ethane / Ambient temperature 2: 4-dimethylaminopyridine, proton sponge / 1,2-dichloro-ethane / Ambient temperature 3: lithium hydroxide / tetrahydrofuran; methanol; H2O / 95 h / Ambient temperature 4: 83 percent / ceric ammonium nitrate / acetonitrile; H2O View Scheme

1: pyridine; copper diacetate; lead(IV) tetraacetate / benzene / 12 h / 90 °C / |Inert atmosphere 2: 3-chloro-benzenecarboperoxoic acid; sodium hydrogencarbonate / dichloromethane / 5 h / 0 - 20 °C 3: HIO4*2H2O / tetrahydrofuran / 5 h / 0 - 20 °C 4: potassium hydroxide; oxygen; Food Red No. 105 / methanol / 6 h / 0 °C / |Irradiation 5: Jone's reagent / acetone / 0.25 h / 0 °C View Scheme

1: pyridine; copper diacetate; lead(IV) tetraacetate / benzene / 12 h / 90 °C / |Inert atmosphere 2: 3-chloro-benzenecarboperoxoic acid; sodium hydrogencarbonate / dichloromethane / 5 h / 0 - 20 °C 3: HIO4*2H2O / tetrahydrofuran / 5 h / 0 - 20 °C 4: potassium hydroxide; oxygen; Food Red No. 105 / methanol / 6 h / 0 °C / |Irradiation View Scheme