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

Published

Author(s)

Srinivasa Ramisetti, Jorge O. Ona Ruales, Stephen Wise, Shantu Amin, Arun Sharma

Abstract

An efficient synthesis of dibenzo[a,l]tetracene (1) and dibenzo[a,j]tetracene (2) has been developed using 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.
Citation
Polycyclic Aromatic Compounds

Keywords

polycyclic aromatic hydrocarbons, Dibenzo[a, l]tetracene, dibenzo[a, j]tetracene, synthesis, SRM 1597a, coal tar

Citation

Ramisetti, S. , Ona Ruales, J. , Wise, S. , Amin, S. and Sharma, A. (2017), An Efficient Synthesis of Dibenzo[a,l]tetracene and Dibenzo[a,j]tetracene and Their Identification in a Coal Tar Extract, Polycyclic Aromatic Compounds, [online], https://doi.org/10.1080/10406638.2017.1362013 (Accessed April 23, 2024)
Created September 7, 2017, Updated October 12, 2021