lithium iodide in N,N-dimethyl-formamide

2,3-dicyano-5,6-dichloro-p-benzoquinone in benzene 0.25 h; Reflux;

1: 92 percent / Jones reagent / acetone / 0.17 h / 20 °C 2: 99 percent / NaOMe / benzene / 2 h / 20 °C 3: 66 percent / NH2OH*HCl / ethanol; H2O / 1 h / Heating 4: 100 percent / NaOMe / methanol; diethyl ether / 0.75 h / 20 °C 5: 92 percent / DDQ / benzene / 0.5 h / Heating 6: 68 percent / LiI / dimethylformamide / 4 h / Heating View Scheme

1: 97 percent / methanolic KOH / 0.5 h / Heating 2: 92 percent / Jones reagent / acetone / 0.17 h / 20 °C 3: 99 percent / NaOMe / benzene / 2 h / 20 °C 4: 66 percent / NH2OH*HCl / ethanol; H2O / 1 h / Heating 5: 100 percent / NaOMe / methanol; diethyl ether / 0.75 h / 20 °C 6: 92 percent / DDQ / benzene / 0.5 h / Heating 7: 68 percent / LiI / dimethylformamide / 4 h / Heating View Scheme

1: 99 percent / NaOMe / benzene / 2 h / 20 °C 2: 66 percent / NH2OH*HCl / ethanol; H2O / 1 h / Heating 3: 100 percent / NaOMe / methanol; diethyl ether / 0.75 h / 20 °C 4: 92 percent / DDQ / benzene / 0.5 h / Heating 5: 68 percent / LiI / dimethylformamide / 4 h / Heating View Scheme

1: 100 percent / NaOMe / methanol; diethyl ether / 0.75 h / 20 °C 2: 92 percent / DDQ / benzene / 0.5 h / Heating 3: 68 percent / LiI / dimethylformamide / 4 h / Heating View Scheme

2,3-dicyano-5,6-dichloro-p-benzoquinone in benzene 24 h; Reflux;

1: 66 percent / NH2OH*HCl / ethanol; H2O / 1 h / Heating 2: 100 percent / NaOMe / methanol; diethyl ether / 0.75 h / 20 °C 3: 92 percent / DDQ / benzene / 0.5 h / Heating 4: 68 percent / LiI / dimethylformamide / 4 h / Heating View Scheme

1: 92 percent / DDQ / benzene / 0.5 h / Heating 2: 68 percent / LiI / dimethylformamide / 4 h / Heating View Scheme

1: 61 percent / NH2OH*HCl / aq. ethanol 2: 100 percent / sodium methoxide / methanol; diethyl ether 3: 1.) phenylselenenyl chloride, 2.) 30 percent aq. H2O2 / 1.) ethyl acetate, 2.) THF 4: 71 percent / LiI / dimethylformamide View Scheme