Oxidation, bromination, and methylenation of carbazole and (E)-3-(2-phenylethenyl)carbazole with HBr/DMSO

M. S. Yusubov, E. A. Krasnokutskaya, V. D. Filimovov, L. F. Kovaleva

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish
Pages (from-to)1260-1263
Number of pages4
JournalChemistry of Heterocyclic Compounds
Volume28
Issue number11
DOIs
Publication statusPublished - Nov 1992

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Dimethyl Sulfoxide
Carbazoles
Oxidation
Methane
carbazole
N-methylcarbazole

ASJC Scopus subject areas

  • Organic Chemistry

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Oxidation, bromination, and methylenation of carbazole and (E)-3-(2-phenylethenyl)carbazole with HBr/DMSO. / Yusubov, M. S.; Krasnokutskaya, E. A.; Filimovov, V. D.; Kovaleva, L. F.

In: Chemistry of Heterocyclic Compounds, Vol. 28, No. 11, 11.1992, p. 1260-1263.

Research output: Contribution to journalArticle

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abstract = "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.",
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AU - Filimovov, V. D.

AU - Kovaleva, L. F.

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AB - 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.

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