Oxidation, bromination, and methylenation of carbazole and (E)-3-(2-phenylethenyl)carbazole with HBr/DMSO
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It is shown that oxidation of (E)-3-(2-phenylethenyl)-9-methylcarbazole with HBr/DMSO leads to the formation of 1-(6-bromo-9-methylcarbazol-3-yl)-2-phenylethane-1,2-dione. In the case of (E)-3-(2-phenylethenyl)carbazole, methylenation occurs with formation of 9,9′-bis[3-(2-phenylethane-1,2-dionyl)-6-bromocarbazolyl]methane in addition to oxidation of the double bond and bromination of the phenyl ring. This reagent can also be successfully used for the preparative bromination and methylenation of certain carbazoles.
KeywordsOxidation Methane Organic Chemistry Phenyl Double Bond
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