Solvolysis of 1-Phenylethyl Tosylates Having Electron-Attracting Substituents

Abstract

Richard et al have determined the lifetime of ring-substituted 1-phenylethyl cations in 50/50 water/trifluoroethanol (I = 0.5, NaClO₄) by use of azid clock, and discussed the mechanistic transition from S_N1 to S_N2 based on the lifetime of these cations. The 1-phenylethyl cation having nitro group has very short lifetime. We are interested in the existence of such an unstable carbocation. Then, we have discussed the solvolysis mechanism of 1-phenylethyl tosylates having electron-withdrawing substituents based on ^-18O-scrambling of starting tosylate during solvolysis.