Reactivity of δ-Functionalized Para-Quinone Methides in Nucleophilic Addition Reactions.

ABSTRACT: The electrophilic reactivities of para-quinone methides (pQMs) with functional groups (FG) at the exocyclic polarized carbon-carbon double bond were determined by photometrically monitoring the kinetics of their reactions with carbanions in dimethyl sulfoxide (DMSO) at 20 °C. The experimental second-order rate constants k₂ were evaluated by the Mayr-Patz equation, that is, the linear free energy relationship lg k₂ = s_N(N + E), which was leveraged to determine the electrophilicity descriptors E of the pQMs. These electrophilicity parameters E were subsequently used to successfully predict the scope of the pQM reactions with C-, H-, N-, O-, and S-centered nucleophiles. Moreover, the electrophilicity parameters E correlate linearly with a linear combination of

SUBMITTER: Gross C 

PROVIDER: S-EPMC12272005 | biostudies-literature | 2025 Jul

REPOSITORIES: biostudies-literature