Fluoroaconitates: Wittig Reaction of Oxalofluoroacetic Acid Esters

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• Mild conditions were necessary since addition on the double bond was observed in aqueous acidic medium as well as cis → trans isomerisation. A basic medium was excluded because of isomerisation to products of type 4. The trans isomer 3cc could be cleaved easily to trans α fluoroaconitic acid. However until now all the attempts to cleave the cis isomer failed. Surprisingly, the mixed ester 3ac (cis) could be cleaved nicely to the cis diacid. HO2C-CHF-C(CO2H)[dbnd]CH-CO2C2H5 without isomerisation
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