2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium t-butanolate 1.) t-BuOH, reflux, 18 h, 2.) dioxane, reflux, 3 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium t-butanolate 1.) t-BuOH, reflux, 18 h, 2.) dioxane, reflux, 3 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

1: 1.) t-BuONa, 2.) DDQ / 1.) t-BuOH, reflux, 18 h, 2.) dioxane, reflux, 3 h 2: 1.) Na, liq. NH3, EtOH, 2.) AcOH / 1.) THF, 18 h, 2.) 100 deg C, overnight 3: 1.) t-BuONa, 2.) DDQ / 1.) t-BuOH, reflux, 15 h, 2.) dioxane, reflux, 15 h 4: 29 mg / I2 / benzene / 12 h / Heating 5: 5percent aq. NaOH / tetrahydrofuran; methanol / 8 h / Ambient temperature 6: pyridine 7: 1.) AIBN, dibromantin, 2.) Li2CO3, LiF / 1.) CCl4, reflux, 30 min, 2.) HMPA, 100 deg C, 3 h 8: 76 percent / NH3 / methanol; tetrahydrofuran / 1.5 h View Scheme