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THE MILD FLUORINATION OF NITROGEN COMPOUNDS
Final rept. 1 Sep 1962-31 Aug 1965
BOSTON COLL CHESTNUT HILL MA DEPT OF CHEMISTRY
Pagination or Media Count:
In an attempt to prepare tetrafluoro hydrazine, or other nitrogen fluorides, the electrolysis of molten hydrazinium difluoride led to the formation of nitrogen gas as the principal anodic product. A trace of nitrogen trifluoride was the sole nitrogen fluoride observed. In a search for a non- aqueous solvent other than hydrogen fluoride in which electrolytic fluorination may be conducted, it was found that the electrolysis of glacial acetic acid solutions of potassium hydrogen fluoride did not lead to fluorination, as had been previously claimed, but to acetoxylation. Thus, 1, 1- diphenylethylene gave the corresponding diacetate, not the difluoride. The possible mechanisms for the acetoxylations involve either the attack of the unsaturated hydrocarbon by acetoxyl radicals, produced at the anode, or nucleophilic attack of cationic species, formed by anodic oxidation of the hydrocarbon. Preliminary evidence that the latter mechanism is operative supports the view that anodic fluorination in a non-aqueous solvent is feasible. The study of the use of acetonitrile as a solvent was also begun. The absence of a suitable soluble fluoride containing electrolyte severly limited its use.
APPROVED FOR PUBLIC RELEASE