An Efficient Synthesis of Dibenzo[a,l]tetracene and Dibenzo[a,j]tetracene and Their Identification in a Coal Tar Extract

Srinivasa R. Ramisetti, Jorge Ona Ruales, Stephen A. Wise, Shantu Amin, Arun K. Sharma

Research output: Contribution to journalArticlepeer-review

Abstract

An efficient synthesis of potentially carcinogenic dibenzo[a,l]tetracene 1 and dibenzo[a,j]tetracene 2 has been developed and the synthetic standards were used to establish their environmental presence. The synthesis involves Diels–Alder reaction of in situ generated ortho-quinodimethane with phenanthrene-1,4-dione, followed by reductive aromatization as key steps. This synthetic strategy resulted in good overall yield and the mixture of 1 and 2 is easily separable by reversed-phase liquid chromatography (RP-LC). Compounds 1 and 2 were identified in a complex mixture of polycyclic aromatic hydrocarbons from coal tar (Standard Reference Material 1597a) and thus could be potential environmental hazards.

Original languageEnglish
Pages (from-to)1-11
Number of pages11
JournalPolycyclic Aromatic Compounds
DOIs
Publication statusAccepted/In press - Sep 8 2017

Keywords

  • Coal tar extract
  • dibenzo[a,j]tetracene
  • dibenzo[a,l]tetracene
  • diels–Alder reaction
  • environmental hazards
  • polycyclic aromatic hydrocarbons

ASJC Scopus subject areas

  • Polymers and Plastics
  • Organic Chemistry
  • Materials Chemistry

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