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

Published: September 08, 2017


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


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
Pub Type: Journals

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polycyclic aromatic hydrocarbons, Dibenzo[a, l]tetracene, dibenzo[a, j]tetracene, synthesis, SRM 1597a, coal tar
Created September 08, 2017, Updated September 27, 2017