Anodic oxidation of benzo[a]pyrene (I) in the presence of pyridine or 4-picoline results in the formation of the 6-(N-pyridinium) and 6-(N-picolinium) derivatives in high yield; the corresponding reaction using 1-methyl-imidazole also results in oxidative coupling but the methylimidazolium residue appears to be bonded to benzo[a]pyrene at C-1.
G. M. Blackburn and J. P. Will, J. Chem. Soc., Chem. Commun., 1974, 67 DOI: 10.1039/C39740000067
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