Skip to main content
eScholarship
Open Access Publications from the University of California
Refine Search

UCLA

UCLA Previously Published Works bannerUCLA

Hyperconjugative Antiaromaticity Activates 4H‑Pyrazoles as Inverse-Electron-Demand Diels–Alder Dienes

Published Web Location

https://doi.org/10.1021/acs.orglett.9b03351
Abstract

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.

Many UC-authored scholarly publications are freely available on this site because of the UC's open access policies. Let us know how this access is important for you.


Top