Preparation of Oxygen-Fluorine Bonds

Trifluoromethyl hypofluorite was first made by Cady by passing methanol [184] or carbon monoxide [185, 186] with fluorine over silver difluoride at elevated temperatures. Later, trifluoromethyl hypofluorite and higher perfluoroalkyl hypofluorites were prepared by treating the appropriate carbonyl compound with fluorine in the presence of dry caesium fluoride at sub-zero temperatures (Fig. 81) [187-189]. 

More recently, Rozen found that treating suspensions of sodium or potassium perfluorocarboxylates with fluorine in an inert solvent, such as trichlorofluoro-methane, afforded oxidising solutions which proved to be mixtures of hypofluorites (Fig.82) [190-192]. 

Of the hypofluorites mentioned above, only the chemistry of the trifluoro-methyl, trifluoroacetyl and acetyl compounds has been explored seriously. These compounds have been used as sources of electrophilic fluorine and details of this chemistry can be found in reviews which have appeared over the years and in the primary literature to which they refer [6, 12, 13, 18, 123, 196-199]. 

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