The β Effect of Silicon in Phenyl Cations

V Dichiarante, A Salvaneschi, S Protti…

Index: Dichiarante, Valentina; Salvaneschi, Andrea; Protti, Stefano; Dondi, Daniele; Fagnoni, Maurizio; Albini, Angelo Journal of the American Chemical Society, 2007 ,  vol. 129,  # 51  p. 15919 - 15926

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Citation Number: 18

Abstract

Irradiation of chloroanisoles, phenols, and N, N-dimethylanilines bearing a trimethylsilyl (TMS) group in the ortho position with respect to the chlorine atom caused photoheterolysis of the Ar-Cl bond and formation of the corresponding ortho-trimethylsilylphenyl cations in the triplet state. The β effect of silicon on these intermediates has been studied by comparing the resulting chemistry in alcoholic solvents with that of the silicon-free analogues and by ...