Formation and stability of ring-substituted 1-phenylethyl carbocations

JP Richard, ME Rothenberg…

Index: Richard, John P.; Rothenberg, Marc E.; Jencks, William P. Journal of the American Chemical Society, 1984 , vol. 106, # 5 p. 1361 - 1372

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Citation Number: 184

Abstract

Abstract: The solvolysis of 1-phenylethyl derivatives with electron-donating 4-substituents in 5050 trifluoroethano1: water (v: v) occurs at a rate that is independent of azide concentration but gives yields of the corresponding azide adducts of up to 98% by trapping a carbocation intermediate. Rate constants for reactions of the cations with solvent range from 2 X lo3 s-'(4- Me2N) to 4 X lo9 s-'(4-Me), assuming a diffusion-controlled rate constant of 5 X lo9 M-'s-' ...