Three of the most important �offspring� of elemental fluorine are acetyl hypofluorite (electrophilic fluorination), bromine trifluoride (nucleophilic fluorination) and HOF�CH3CN complex (electrophilic oxygenation). Acetyl hypofluorite, made easily from diluted fluorine and AcONa is very efficient in fluorinating anionic centers. Compounds containing the moieties -CH2SO2- or   -COCH2PO- reacted with AcOF to produce the mono or difluoro -CFYSO2- or -COCFYPO- derivatives (Y = H or F) at will. BrF3 and BrF3�Py are excellent tools for constructing both CF2 and CF3 groups, the latter useful when aromatic rings are part of the substrate. An important option is its ability to lead to Ar-CF2[18]F compounds. HOF�CH3CN has many rolls in the oxygen transfer chemistry. As time permits, we will describe the incorporation of the 18O isotope to form the N-oxide group of the benzotriazine skeleton which is so important in cancer therapy.

Versatile nature of elemental fluorine

245th National Meeting (2013)

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