Substitution of a Carbon-Fluorine Bond

Thermolysis of p-tolyl (or / -anisyl) azide in perfluoronaphthalene under nitrogen gives a low yield of the corresponding JV-aryl-1-heptafluoronaphthylamine (44).  

Formation of a 1- rather than a 2-substituted perfluoronaphthalene derivative is suggestive of a radical rather than simple nucleophilic attack by a preformed amine. The total suppression of the formation of 44 when the experiment was carried out in the presence of oxygen lends further support to the intervention of a triplet reaction. 

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Laot Y, Petit L, Zard SZ (2010) Synthesis of fluoroazaindohnes by an uncommon radical ipso substitution of a carbon- fluorine bond. Org Lett 12 3426-3429... 

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