Formation and chlorination of carbazole, phenoxazine, and phenazine

Mohammednoor Altarawneh, Bogdan Z. Dlugogorski

Research output: Contribution to journalArticlepeer-review

65 Citations (Scopus)


This contribution presents pathways for the formation of the three nitrogenated dioxin-like species, carbazole, phenoxazine, and phenazine via unimolecular rearrangements of diphenylamine (DPA) and its nitro substituents (NDPA). The latter represent major structural entities appearing in formulations of explosives and propellants. Intramolecular H transfer from the amine group to one of the two O atoms in the nitro group denotes the most accessible route in the unimolecular decomposition of NDPA. Further unimolecular rearrangements afford phenazine and carbazole. A loss of an ortho substituent from DPA, followed by addition of an oxygen molecule, prompts the formation of carbazole and phenoxazine in a facile mechanism. The consistency between trends in Fukui-based electrophilic indices and the experimental profiles of chlorinated carbazole, phenoxazine, and phenazine suggests the formation of these species by electrophilic substitution.

Original languageEnglish
Pages (from-to)2215-2221
Number of pages7
JournalEnvironmental Science and Technology
Issue number4
Publication statusPublished - Feb 17 2015
Externally publishedYes

ASJC Scopus subject areas

  • General Chemistry
  • Environmental Chemistry


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