The use of an isobasic plot shows that, when structures are analogous and pKa values identical, RO– departs from acetoacetate ester anions 5 × 103 times faster than RS– and 79 times faster from fluorene-9-carboxylic acid ester anions, a reversal of the apparent order of nucleofugality determined by measured rates of elimination of RS– and RO–.
K. T. Douglas and M. Alborz, J. Chem. Soc., Chem. Commun., 1981, 551 DOI: 10.1039/C39810000551
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