Synthesis of regiospecifically fluorinated polycyclic aromatic hydrocarbons

ORGN 775

Shaibal Banerjee,, Saikat Sinha,, and Barbara Zajc, Department of Chemistry, The City College and The City University of New York, 160 Convent Avenue, New York, NY 10031
Regiospecifically fluorinated PAHs have been prepared via fluoro-Julia olefination, followed by photochemical ring closure of the resulting fluorostilbene derivatives. Using this approach, the regioisomeric pairs 5-fluoro and 6-fluoro-benzo[c]phenanthrene, 5-fluoro and 6-fluoro-chrysene, as well as 9-fluoro and 10-fluoro-benzo[g]chrysene have been synthesized.