2,3-dicyano-5,6-dichloro-p-benzoquinone in 1,4-dioxane T=100°C; 1.5 h;

1: 55 percent / Botryodiplodia malorum / 40 h 2: 65 percent / dimethylaminopyridine / pyridine / 72 h / Ambient temperature 3: 98 percent / tert-butylhydroperoxide, VO(C5H7O2)2 / toluene / 2 h / 80 °C 4: 79 percent / P(C6H5)3 / CCl4; CH2Cl2; pyridine / 2 h / 0 deg C to room temp. 5: 75 percent / Zn / acetic anhydride; tetrahydrofuran / 1.5 h / 70 °C 6: 94 percent / KOH, NaClO4 / tetrahydrofuran; methanol / 2.5 h / Ambient temperature 7: 88 percent / Zn/Cu / 1,2-dimethoxy-ethane / 5 h / 55 °C 8: 69 percent / KOEt / tetrahydrofuran / 2 h / Ambient temperature 9: 95 percent / H2 / Pd/CaCO3 / tetrahydrofuran; propan-2-ol / 2 h / 750.06 Torr / Ambient temperature 10: 62 percent / pyridinium dichromate / dimethylformamide / 24 h / 70 °C 11: 59 percent / DDQ / dioxane / 1.5 h / 100 °C View Scheme

1: 69 percent / KOEt / tetrahydrofuran / 2 h / Ambient temperature 2: 95 percent / H2 / Pd/CaCO3 / tetrahydrofuran; propan-2-ol / 2 h / 750.06 Torr / Ambient temperature 3: 62 percent / pyridinium dichromate / dimethylformamide / 24 h / 70 °C 4: 59 percent / DDQ / dioxane / 1.5 h / 100 °C View Scheme

1: 88 percent / Zn/Cu / 1,2-dimethoxy-ethane / 5 h / 55 °C 2: 69 percent / KOEt / tetrahydrofuran / 2 h / Ambient temperature 3: 95 percent / H2 / Pd/CaCO3 / tetrahydrofuran; propan-2-ol / 2 h / 750.06 Torr / Ambient temperature 4: 62 percent / pyridinium dichromate / dimethylformamide / 24 h / 70 °C 5: 59 percent / DDQ / dioxane / 1.5 h / 100 °C View Scheme

1: 65 percent / dimethylaminopyridine / pyridine / 72 h / Ambient temperature 2: 98 percent / tert-butylhydroperoxide, VO(C5H7O2)2 / toluene / 2 h / 80 °C 3: 79 percent / P(C6H5)3 / CCl4; CH2Cl2; pyridine / 2 h / 0 deg C to room temp. 4: 75 percent / Zn / acetic anhydride; tetrahydrofuran / 1.5 h / 70 °C 5: 94 percent / KOH, NaClO4 / tetrahydrofuran; methanol / 2.5 h / Ambient temperature 6: 88 percent / Zn/Cu / 1,2-dimethoxy-ethane / 5 h / 55 °C 7: 69 percent / KOEt / tetrahydrofuran / 2 h / Ambient temperature 8: 95 percent / H2 / Pd/CaCO3 / tetrahydrofuran; propan-2-ol / 2 h / 750.06 Torr / Ambient temperature 9: 62 percent / pyridinium dichromate / dimethylformamide / 24 h / 70 °C 10: 59 percent / DDQ / dioxane / 1.5 h / 100 °C View Scheme

1: 95 percent / H2 / Pd/CaCO3 / tetrahydrofuran; propan-2-ol / 2 h / 750.06 Torr / Ambient temperature 2: 62 percent / pyridinium dichromate / dimethylformamide / 24 h / 70 °C 3: 59 percent / DDQ / dioxane / 1.5 h / 100 °C View Scheme

1: 94 percent / KOH, NaClO4 / tetrahydrofuran; methanol / 2.5 h / Ambient temperature 2: 88 percent / Zn/Cu / 1,2-dimethoxy-ethane / 5 h / 55 °C 3: 69 percent / KOEt / tetrahydrofuran / 2 h / Ambient temperature 4: 95 percent / H2 / Pd/CaCO3 / tetrahydrofuran; propan-2-ol / 2 h / 750.06 Torr / Ambient temperature 5: 62 percent / pyridinium dichromate / dimethylformamide / 24 h / 70 °C 6: 59 percent / DDQ / dioxane / 1.5 h / 100 °C View Scheme

1: 79 percent / P(C6H5)3 / CCl4; CH2Cl2; pyridine / 2 h / 0 deg C to room temp. 2: 75 percent / Zn / acetic anhydride; tetrahydrofuran / 1.5 h / 70 °C 3: 94 percent / KOH, NaClO4 / tetrahydrofuran; methanol / 2.5 h / Ambient temperature 4: 88 percent / Zn/Cu / 1,2-dimethoxy-ethane / 5 h / 55 °C 5: 69 percent / KOEt / tetrahydrofuran / 2 h / Ambient temperature 6: 95 percent / H2 / Pd/CaCO3 / tetrahydrofuran; propan-2-ol / 2 h / 750.06 Torr / Ambient temperature 7: 62 percent / pyridinium dichromate / dimethylformamide / 24 h / 70 °C 8: 59 percent / DDQ / dioxane / 1.5 h / 100 °C View Scheme

1: 75 percent / Zn / acetic anhydride; tetrahydrofuran / 1.5 h / 70 °C 2: 94 percent / KOH, NaClO4 / tetrahydrofuran; methanol / 2.5 h / Ambient temperature 3: 88 percent / Zn/Cu / 1,2-dimethoxy-ethane / 5 h / 55 °C 4: 69 percent / KOEt / tetrahydrofuran / 2 h / Ambient temperature 5: 95 percent / H2 / Pd/CaCO3 / tetrahydrofuran; propan-2-ol / 2 h / 750.06 Torr / Ambient temperature 6: 62 percent / pyridinium dichromate / dimethylformamide / 24 h / 70 °C 7: 59 percent / DDQ / dioxane / 1.5 h / 100 °C View Scheme

1: 98 percent / tert-butylhydroperoxide, VO(C5H7O2)2 / toluene / 2 h / 80 °C 2: 79 percent / P(C6H5)3 / CCl4; CH2Cl2; pyridine / 2 h / 0 deg C to room temp. 3: 75 percent / Zn / acetic anhydride; tetrahydrofuran / 1.5 h / 70 °C 4: 94 percent / KOH, NaClO4 / tetrahydrofuran; methanol / 2.5 h / Ambient temperature 5: 88 percent / Zn/Cu / 1,2-dimethoxy-ethane / 5 h / 55 °C 6: 69 percent / KOEt / tetrahydrofuran / 2 h / Ambient temperature 7: 95 percent / H2 / Pd/CaCO3 / tetrahydrofuran; propan-2-ol / 2 h / 750.06 Torr / Ambient temperature 8: 62 percent / pyridinium dichromate / dimethylformamide / 24 h / 70 °C 9: 59 percent / DDQ / dioxane / 1.5 h / 100 °C View Scheme