SELECTIVE AND EFFICIENT DIRECT FLUORINATION OF POLYCYCLIC AROMATIC-HYDROCARBONS USING -FLUORO-4-HYDROXY-1,4-DIAZONIABICYCLO[2.2.2]OCTANE BIS(TETRAFLUOROBORATE)

A new N-F fluorinating reagent -fluoro-4-hydroxy-1,4-diazoniabicyclo[2 .2.2]octane bis(tetrafluoroborate) (Accufluor(TM) NFTh) was effectivel y used for selective fluorination of polycyclic aromatics. Naphthalene was site-selectively fluorinated to 1-fluoronaphthalene, phenanthrene to 9-fluorophenanthrene, and pyrene to 1-fluoropyrene. In a series of substituted naphthalenes the regioselectivity and effectiveness of fl uorination depended on the position and the nature of the substituents .