Convenient criterion for the distinction between electrophilic and electron transfer reactions of electron??rich alkenes

…, JT Aplin, W Yueh, S Endo, A Loving

Index: Bauld, Nathan L.; Aplin, J. Todd; Yueh, Wang; Endo, Stephanie; Loving, Angie Journal of Physical Organic Chemistry, 1998 , vol. 11, # 1 p. 15 - 24

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Citation Number: 13

Abstract

Abstract Both experimental and theoretical studies confirm that the formation of aryl vinyl ether and aryl vinyl sulfide cation radicals from the corresponding neutral substrates correlates with the Brown σ+ parameters as opposed to Hammett σ values. Peak oxidation potentials for both classes of substrates correlate preferentially with σ+, as do gas-phase ionization energies calculated by both semi-empirical and ab initio methods. In contrast, ...