Electrophilic Reactivities of Vinyl p‑Quinone Methides

Electrophilic Reactivities of Vinyl p‑Quinone Methides

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 us...

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Veröffentlicht in:Organic letters 2020-03, Vol.22 (6), p.2182-2186
Hauptverfasser: Eitzinger, Andreas, Mayer, Robert J, Hampel, Nathalie, Mayer, Peter, Waser, Mario, Ofial, Armin R
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Sprache:eng
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c00338