2,3-dicyano-5,6-dichloro-p-benzoquinone in 1,4-dioxane Heating;

1: 1.) NaH / 1) THF, 0 deg C, 2) THF, RT, 1 h 2: 95 percent / chlorobenzene / 16.5 h / Heating 3: 63 percent Turnov. / 2,3-dicloro-5,6-dicyano-1,4-benzoquinone / dioxane / 6 h / Heating View Scheme

1: 71 percent / 80percent m-chloroperbenzoic acid / CH2Cl2 / 3 h / Ambient temperature 2: 1.) NaH / 1) THF, 0 deg C, 2) THF, RT, 1 h 3: 95 percent / chlorobenzene / 16.5 h / Heating 4: 63 percent Turnov. / 2,3-dicloro-5,6-dicyano-1,4-benzoquinone / dioxane / 6 h / Heating View Scheme

1: 81 percent 2: 71 percent / mcpba 3: 67 percent / tetrahydrofuran / Ambient temperature 4: 95 percent / chlorobenzene / 132 °C 5: 63 percent / DDQ / dioxane / Heating View Scheme

in tetrahydrofuran 2 h; Ambient temperature;