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| - Synthesis of α-Fluorocarboxylates from the Corresponding AcidsUsing Acetyl Hypofluorite
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| - α-Fluorocarboxylic esters and acids were synthesized in good yields. The corresponding esters andacids were converted to their ketene acetals, and these enol derivatives reacted with AcOF madedirectly from fluorine. This route circumvents the problems associated with nucleophilic fluorinationssuch as various eliminations and rearrangements. α- and β-branched carboxylic acid derivativesthat cannot be directly fluorinated gave by this electrophilic fluorination the corresponding α-fluoroderivatives in good yield. Both the fluorination reaction and the preparation of AcOF are fast andsuitable for [18]F incorporation into acids and esters needed for working with PET. α-Fluoroibuprofen (20) and methyl 2-fluoro-3,3,3-triphenylpropionate (32) are two examples of this generalreaction.
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