Bonding of benzo[a]pyrene to nitrogen heterocycles by anodic oxidation

Abstract

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.