dipotassium hydrogenphosphate; Fremy’s salt in water; acetone 4 h;

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: 80 percent / pyridinium chlorochromate / CH2Cl2 / 96 h / Ambient temperature 10: 82 percent / NaBH4 / ethanol / 1 h / Ambient temperature 11: 42 percent / CH3SO2Cl, Et3N / CH2Cl2 / 0 °C 12: 77 percent / NaH, EtSH / dimethylformamide / 3 h / 150 °C 13: 57 percent / potassium nitrosodisulfonate, potassium hydrogen phosphate / H2O; acetone / 4 h 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: 80 percent / pyridinium chlorochromate / CH2Cl2 / 96 h / Ambient temperature 9: 82 percent / NaBH4 / ethanol / 1 h / Ambient temperature 10: 42 percent / CH3SO2Cl, Et3N / CH2Cl2 / 0 °C 11: 77 percent / NaH, EtSH / dimethylformamide / 3 h / 150 °C 12: 57 percent / potassium nitrosodisulfonate, potassium hydrogen phosphate / H2O; acetone / 4 h View Scheme

1: 69 percent / Zn / tetrahydrofuran / 2 h 2: 62 percent / Pd-black / 2 h / 280 - 300 °C 3: 1) Mg / 1) Et2O, 30 min 2) Et2O, 3h 4: P2O5, H3PO4 / 0.5 h / 60 - 70 °C 5: 80 percent / pyridinium chlorochromate / CH2Cl2 / 96 h / Ambient temperature 6: 82 percent / NaBH4 / ethanol / 1 h / Ambient temperature 7: 42 percent / CH3SO2Cl, Et3N / CH2Cl2 / 0 °C 8: 77 percent / NaH, EtSH / dimethylformamide / 3 h / 150 °C 9: 57 percent / potassium nitrosodisulfonate, potassium hydrogen phosphate / H2O; acetone / 4 h 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: 80 percent / pyridinium chlorochromate / CH2Cl2 / 96 h / Ambient temperature 7: 82 percent / NaBH4 / ethanol / 1 h / Ambient temperature 8: 42 percent / CH3SO2Cl, Et3N / CH2Cl2 / 0 °C 9: 77 percent / NaH, EtSH / dimethylformamide / 3 h / 150 °C 10: 57 percent / potassium nitrosodisulfonate, potassium hydrogen phosphate / H2O; acetone / 4 h 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: 80 percent / pyridinium chlorochromate / CH2Cl2 / 96 h / Ambient temperature 8: 82 percent / NaBH4 / ethanol / 1 h / Ambient temperature 9: 42 percent / CH3SO2Cl, Et3N / CH2Cl2 / 0 °C 10: 77 percent / NaH, EtSH / dimethylformamide / 3 h / 150 °C 11: 57 percent / potassium nitrosodisulfonate, potassium hydrogen phosphate / H2O; acetone / 4 h 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: 80 percent / pyridinium chlorochromate / CH2Cl2 / 96 h / Ambient temperature 5: 82 percent / NaBH4 / ethanol / 1 h / Ambient temperature 6: 42 percent / CH3SO2Cl, Et3N / CH2Cl2 / 0 °C 7: 77 percent / NaH, EtSH / dimethylformamide / 3 h / 150 °C 8: 57 percent / potassium nitrosodisulfonate, potassium hydrogen phosphate / H2O; acetone / 4 h View Scheme

1: 51 percent / DDQ / benzene / 12 h / Heating 2: ethanol / 15 h / Ambient temperature 3: 83 percent / n-BuLi / diethyl ether; hexane 4: NaH, ethanethiol / dimethylformamide / 10 h / 130 °C 5: (NH4)2Ce(NO3)6 / acetonitrile; H2O View Scheme

1: NaH, ethanethiol / dimethylformamide / 10 h / 130 °C 2: (NH4)2Ce(NO3)6 / acetonitrile; H2O View Scheme

1: ethanol / 15 h / Ambient temperature 2: 83 percent / n-BuLi / diethyl ether; hexane 3: NaH, ethanethiol / dimethylformamide / 10 h / 130 °C 4: (NH4)2Ce(NO3)6 / acetonitrile; H2O View Scheme