Hyperconjugative Antiaromaticity Activates 4-Pyrazoles as Inverse-Electron-Demand Diels-Alder Dienes.

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ID: 64013
2019
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Abstract
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.
Reference Key
levandowski2019hyperconjugativeorganic Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Levandowski, Brian J;Abularrage, Nile S;Houk, K N;Raines, Ronald T;
Journal Organic letters
Year 2019
DOI
10.1021/acs.orglett.9b03351
URL
Keywords
toxicity biological azoles microbial inhibition

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