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Electrophilic Reactivities of Vinyl p-Quinone Methides.


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

SUBMITTER: Eitzinger A 

PROVIDER: S-EPMC7091536 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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

Eitzinger Andreas A   Mayer Robert J RJ   Hampel Nathalie N   Mayer Peter P   Waser Mario M   Ofial Armin R AR  

Organic letters 20200302 6


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<sub>N</sub>(<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. ...[more]

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