silver(l) oxide in ethanol T=24°C; 3 h; ultrasonication;

dipotassium hydrogenphosphate; Fremy’s salt in water; acetone

1.1: hydroxylamine hydrochloride; aq. NaOH / methanol / 4 h / Heating 2.1: 16.9 g / acetic anhydride; acetic acid; hydrogen chloride / 100 °C 3.1: sodium nitrite; aq. HCl / 0.5 h / 0 °C 3.2: 40 percent / CuCl; aq. HCl / 0 - 75 °C 4.1: 97.53 percent / NiCl2(dppp) / diethyl ether 5.1: 100 percent / AlCl3 / CH2Cl2 / 0.5 h / 0 °C 6.1: boron tribromide / CH2Cl2 / 2 h / 20 °C 7.1: 0.8 g / Dess-Martin periodinane / CH2Cl2 / 20 °C View Scheme

1: 87 percent / 20percent aq. NaOH / 2 h / Heating 2: 53 percent / AlCl3 / nitrobenzene / Ambient temperature 3: 53 percent / Zn, HgCl2, conc. HCl / H2O; toluene / 24 h / Heating 4: 81 percent / P2O5, H3PO4 / CH2Cl2 / 0.33 h / 70 - 80 °C 5: 69 percent / Zn / tetrahydrofuran / 2 h 6: 62 percent / Pd-black / 2 h / 280 - 300 °C 7: 1) Mg / 1) Et2O, 30 min 2) Et2O, 3h 8: P2O5, H3PO4 / 0.5 h / 60 - 70 °C 9: 86 percent / BBr3 / CH2Cl2 / 1 h / Ambient temperature 10: 40 percent / Potassium nitrosodisulfonate, potassium hydrogen phosphate / acetone; H2O View Scheme

1: 53 percent / AlCl3 / nitrobenzene / Ambient temperature 2: 53 percent / Zn, HgCl2, conc. HCl / H2O; toluene / 24 h / Heating 3: 81 percent / P2O5, H3PO4 / CH2Cl2 / 0.33 h / 70 - 80 °C 4: 69 percent / Zn / tetrahydrofuran / 2 h 5: 62 percent / Pd-black / 2 h / 280 - 300 °C 6: 1) Mg / 1) Et2O, 30 min 2) Et2O, 3h 7: P2O5, H3PO4 / 0.5 h / 60 - 70 °C 8: 86 percent / BBr3 / CH2Cl2 / 1 h / Ambient temperature 9: 40 percent / Potassium nitrosodisulfonate, potassium hydrogen phosphate / acetone; H2O View Scheme

1: 81 percent / P2O5, H3PO4 / CH2Cl2 / 0.33 h / 70 - 80 °C 2: 69 percent / Zn / tetrahydrofuran / 2 h 3: 62 percent / Pd-black / 2 h / 280 - 300 °C 4: 1) Mg / 1) Et2O, 30 min 2) Et2O, 3h 5: P2O5, H3PO4 / 0.5 h / 60 - 70 °C 6: 86 percent / BBr3 / CH2Cl2 / 1 h / Ambient temperature 7: 40 percent / Potassium nitrosodisulfonate, potassium hydrogen phosphate / acetone; H2O View Scheme

1: 53 percent / Zn, HgCl2, conc. HCl / H2O; toluene / 24 h / Heating 2: 81 percent / P2O5, H3PO4 / CH2Cl2 / 0.33 h / 70 - 80 °C 3: 69 percent / Zn / tetrahydrofuran / 2 h 4: 62 percent / Pd-black / 2 h / 280 - 300 °C 5: 1) Mg / 1) Et2O, 30 min 2) Et2O, 3h 6: P2O5, H3PO4 / 0.5 h / 60 - 70 °C 7: 86 percent / BBr3 / CH2Cl2 / 1 h / Ambient temperature 8: 40 percent / Potassium nitrosodisulfonate, potassium hydrogen phosphate / acetone; H2O View Scheme

1: 62 percent / Pd-black / 2 h / 280 - 300 °C 2: 1) Mg / 1) Et2O, 30 min 2) Et2O, 3h 3: P2O5, H3PO4 / 0.5 h / 60 - 70 °C 4: 86 percent / BBr3 / CH2Cl2 / 1 h / Ambient temperature 5: 40 percent / Potassium nitrosodisulfonate, potassium hydrogen phosphate / acetone; H2O View Scheme

1: boron tribromide / CH2Cl2 / 2 h / 20 °C 2: 0.8 g / Dess-Martin periodinane / CH2Cl2 / 20 °C View Scheme

1: 97.53 percent / NiCl2(dppp) / diethyl ether 2: 100 percent / AlCl3 / CH2Cl2 / 0.5 h / 0 °C 3: boron tribromide / CH2Cl2 / 2 h / 20 °C 4: 0.8 g / Dess-Martin periodinane / CH2Cl2 / 20 °C View Scheme