Electrophilic Attack of Elemental Fluorine on Organic Halogens. Synthesis of Fluoroadamantanes

Elemental fluorine acts on bromo- and iodoadamantanes in an electrophilic mode to produce the corresponding fluoroadamantanes. The course of the reaction was investigated in several solvents. It was found that the best yields of the fluoroadamantanes were obtained when Freon (CFCl₃) or Freon-chloroform was used. Using methylene chloride as a solvent with iodoadamantanes-but not with the bromo derivatives-resulted in considerable amounts of the corresponding chloro compounds.