Electrophilic Reactivities of Vinyl <i>p</i>-Quinone Methides

Abstract

The electrophilic reactivity of a series of 8-arylated vinyl <i>p</i>-quinone methides (<i>p</i>VQMs) was determined by analyzing the kinetics of their reactions with carbanions in DMSO at 20 °C according to the linear free energy relationship log <i>k</i> = s_N(<i>N</i> + <i>E</i>). The electrophilicity parameters <i>E</i> for <i>p</i>VQMs were used to successfully predict Michael-additions with structurally diverse C-, N-, S-, and H-nucleophiles.