oxygen in ethanol 1 h; IrradiationIrradiation in glass or quartz, study of other methods of working up; Product distribution;

ethanol; oxygen; toluene-4-sulfonic acid; orthoformic acid triethyl ester Irradiation; Product distribution;

Irradiationradiolytic degradation; Product distributionRate constant;

Jones's reagent in acetone T=20°C; 0.0833333 h;

sodium tetrahydroborate in pyridine; methanol

1: 48 percent / p-TsOH, triethyl orthoformate / benzene / 8 h / Heating 2: 70 percent / aq. AcOH / Heating 3: 71 percent / NaBH4 / methanol; pyridine View Scheme

p-toluenesulfonic acid monohydrate in ethanol 3 h; Heating / reflux;

1: 90 percent / ethylenediamine / toluene / 2 h 2: 32 percent / ethylenediamine / diethyl ether / 2 h 3: 82 percent / HgSO4 / methanol; tetrahydrofuran / 1.5 h / 20 °C View Scheme

1: benzene 2: und anschliessenden Hydrolisieren View Scheme

1: p-TsOH / benzene / 24 h / Heating 2: 80 percent / mCPBA / CH2Cl2 / 24 h / -20 - 0 °C 3: iPr2NEt / CH2Cl2 / 0.5 h / -78 °C 4: 1) mCPBA, KHCO3, 2) citric acid / 1) CH2Cl2, -30 to -20 deg C, 1 h, 2) MeOH, 0 deg C to RT 5: NaIO4 / methanol; H2O / 0 deg C, 12 h; RT, 3 h 6: CHCl3 / Ambient temperature 7: 71 percent / LTBA / tetrahydrofuran / -78 to -40 deg C; -35 deg C, 4 h 8: 89 percent / nBu3P / tetrahydrofuran / 1 h / 0 - 20 °C 9: 85 percent / 30percent H2O2 / tetrahydrofuran / 18 h / 0 - 20 °C 10: I2, NaHCO3 / CH2Cl2 / 48 h / Ambient temperature 11: 90 percent / methanol / 4 h / 0 - 20 °C 12: LTBA / tetrahydrofuran / 3 h / 0 °C 13: pyridine / 2 h / 0 - 20 °C 14: 56 percent / CSA, dihydroquinone / benzene / 3 h / Heating 15: 1) mCPBA, 2) 2N HCl / 1) CH2Cl2, -30 to -25 deg C, 20 h, 2) THF, RT, 16 h 16: Me4NBH(OAc)3 / acetic acid; acetonitrile / 2 h / 0 °C 17: DDQ / dioxane / 4 h / 80 °C 18: 94 percent / Ag2O / acetonitrile / 24 h / Ambient temperature 19: 92 percent / MsCl, Et3N / CH2Cl2 / Ambient temperature 20: 47 percent / OsO4, DABCO / tetrahydrofuran / 24 h / -40 °C 21: 92 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 16 h / Ambient temperature 22: CH(NMe2)3 / 1 h / 100 °C 23: 2N HCl / tetrahydrofuran / 20 h / Ambient temperature 24: PCC / CH2Cl2 / 5 h / Ambient temperature 25: CH2Cl2 / 0.33 h / Ambient temperature 26: DBN / CH2Cl2 / 6 h / Ambient temperature 27: K2CO3, MeOH / 5 h / Ambient temperature 28: 1N HCl / tetrahydrofuran / 12 h / Ambient temperature 29: 49 percent / pyridine / 12 h / -20 °C 30: 73 percent / PCC / CH2Cl2 / 2 h / Ambient temperature View Scheme