Hyperconjugative Antiaromaticity Activates 4-Pyrazoles as Inverse-Electron-Demand Diels-Alder Dienes.
Clicks: 240
ID: 64013
2019
The Diels-Alder reactivity of 4,4-difluoro-3,5-diphenyl-4-pyrazole was investigated experimentally and computationally with -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-4-pyrazoles are new electron-deficient dienes with rapid reactivities toward strained alkynes.
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levandowski2019hyperconjugativeorganic
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| Authors | Levandowski, Brian J;Abularrage, Nile S;Houk, K N;Raines, Ronald T; |
| Journal | Organic letters |
| Year | 2019 |
| DOI | 10.1021/acs.orglett.9b03351 |
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