Abstract
3-(Fluoroacyloxy)quinoline-2,4(1 H,3 H)-diones react with triethyl phosphite to afford either the product of the Perkow reaction or the corresponding 4-ethoxyquinolin-2(1 H)-one. In both reactions, the fluorocarboxylate anion acts as the leaving group. For the corresponding 3-(fluoroiodoacetoxy) derivative this observation precludes the application of the intramolecular Wittig–Horner synthesis to modify quinoline-2,4(1 H,3 H)-diones by the annulation of a fluorinated but-2-enolide moiety.
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