Anchimeric assistance by γ-aryl groups in solvolysis of organosilicon iodides. Some remarkably large remote substituent effects

Abstract

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.