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Triethyl α-Fluoroaconitate

Abstract

THE current theory on the mode of action of fluoroacetate1 implies the lethal synthesis of fluoro-citrate which poisons the enzyme aconitase, thus preventing the catabolism of citrate to aconitate; it seemed of interest to prepare and study α-fluoroaconitic acid, HOOC.CHF.C(COOH)=CH.COOH. Triethyl fluorocitrate, which would appear to be a suitable starting material, has been prepared in a facile reaction, namely, by the Reformatzky reaction between diethyl oxalofluoroacetate and ethyl bromoacetate2, but our attempts to dehydrate this compound failed to give a defined product.

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References

  1. Peters, R. A., “Adv. in Enzymol.”, 18, 13 (Interscience Pub. Inc. New York, 1957).

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  2. Rivett, D. E. A., J. Chem. Soc., 3710 (1953).

  3. Kacser, H., Discuss. Farad. Soc., 20, 289 (1955).

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  4. Blank, I., Mager, J., and Bergmann, E. D., Bull. Res. Council Israel, 3, 101 (1953); J. Chem. Soc., 2180 (1955).

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BERGMANN, E., SHAHAK, I. Triethyl α-Fluoroaconitate. Nature 185, 529–530 (1960). https://doi.org/10.1038/185529b0

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