Abstract

The title compds., useful in the prodn. of dye intermediates, are prepd. in acid media in an electrolysis cell whose electrodes are sepd. by a membrane. At the cathode, anthraquinones are reductively cyclized with glycerol [56-81-5] to give the corresponding benzanthrones. In the anode chamber the oxidn. state of a transition metal ion is electrochem. increased by 1 and the resulting ion serves as a chem. oxidant for a planar polycyclic arom. compd. Thus, to the cathode chamber contg. 46.8 g anthraquinone [84-65-1] in 1300 g H2SO4, 31.05 g glycerol was added dropwise while the current was running. On the anodic side 10 g MnSO4.H2O was suspended in 130 g 88% H2SO4. benzanthrone [82-05-3] (85%) Was isolated from the cathodic portion, while the anolyte was used to cyclooxidize 10 g 4,4'-bibenzanthrone [116-90-5] to dioxoviolanthrone [64346-54-9] which was reduced with NaHSO3 to dihydroxyviolanthrone (I) [26545-62-0] in 76.4% yield. I was used as an intermediate in the synthesis of vat dyes. [on SciFinder (R)]

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