Hyperconjugative Antiaromaticity Activates 4 H -Pyrazoles as Inverse-Electron-Demand Diels–Alder Dienes
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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.
Date issued
2019-10Department
Massachusetts Institute of Technology. Department of ChemistryJournal
Organic Letters
Publisher
American Chemical Society (ACS)
Citation
Levandowski, Brian J. "Hyperconjugative Antiaromaticity Activates 4 H -Pyrazoles as Inverse-Electron-Demand Diels–Alder Dienes." Organic Letters 21, 20 (October 2019): 8492–8495 © 2019 American Chemical Society
Version: Author's final manuscript
ISSN
1523-7052
1523-7060