Acid-Catalyzed Intermolecular Rearrangement of N-Chlorocarbazole

Michael De Rosa, P. Andres Quesada, David J. Dodsworth

Research output: Contribution to journalArticle

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Abstract

The chlorination of carbazole with sodium hypochlorite in CH2Cl2, CHCl3, or CCl4gave N-chlorocarbazole in 63-95% yield. It rearranged in refluxing methanol to give carbazole, 3-chlorocarbazole, 1-chlorocarbazole, 3,6-dichlorocarbazole, and 1,6-dichlorocarbazole. These chlorocarbazoles were formed in an acid-catalyzed intermolecular reaction. In the presence of potassium carbonate dechlorination of N-chlorocarbazole was observed. No evidence for an intramolecular rearrangement was found.

Original languageEnglish (US)
Pages (from-to)173-175
Number of pages3
JournalJournal of Organic Chemistry
Volume52
Issue number2
DOIs
StatePublished - Jan 1 1987

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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