The Journal of Organic Chemistry

Fluorination of polycyclic aromatic hydrocarbons: charge vs. frontier orbital control in substitution reactions of radical cations

PF King, RF O'Malley

Index: King, Patrick F.; O'Malley, Robert F. Journal of Organic Chemistry, 1984 , vol. 49, # 15 p. 2803 - 2807

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Citation Number: 14

Abstract

The anodic fluorination of perylene and pyrene in acetonitrile occurred at potentials consistent with the intermediacy of dications, but that of triphenylene with ita radical cation. Fluorination of anthracene compounds at a meso position occurred by the action of iodine/silver (I) fluoride in acetonitrile via radical cation intermediates. Phenanthrene, 9- nitroanthracene, perylene, and pyrene failed to react. These results support the view that ...