The very large spread of rates in reactions of the iodides (Me3Si)2C(SiMe2C6H4X)(SiMe2l)(X =p-OMe, p-Me, H, p-Cl, or m-CF3) with (CF3)2CHOH and CF3CH2OH (the compound with X =p-OMe is 1.9 × 105 and 6.5 × 104 times, respectively, as reactive as that with X =m-CF3) is attributed to nucleophilic assistance by the aryl group to the leaving of the I– ion.
C. Eaborn, K. L. Jones and P. D. Lickiss, J. Chem. Soc., Chem. Commun., 1989, 595 DOI: 10.1039/C39890000595
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