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Hyperconjugative Antiaromaticity Activates 4H‑Pyrazoles as Inverse-Electron-Demand Diels–Alder Dienes
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https://doi.org/10.1021/acs.orglett.9b03351Abstract
The Diels-Alder reactivity of 4,4-difluoro-3,5-diphenyl-4H-pyrazole was investigated experimentally and computationally with endo-bicyclo[6.1.0]non-4-yne. The computationally predicted rate enhancement from hyperconjugative antiaromaticity induced by fluorination of cyclopentadienes at the 5-position extends to five-membered heterocyclic dienes containing a saturated center. 4,4-Difluoro-4H-pyrazoles are new electron-deficient dienes with rapid reactivities toward strained alkynes.
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