| dc.contributor.author | Levandowski, Brian | |
| dc.contributor.author | Abularrage, Nile S | |
| dc.contributor.author | Houk, KN | |
| dc.contributor.author | Raines, Ronald T | |
| dc.date.accessioned | 2020-11-20T18:37:43Z | |
| dc.date.available | 2020-11-20T18:37:43Z | |
| dc.date.issued | 2019-10 | |
| dc.date.submitted | 2019-09 | |
| dc.identifier.issn | 1523-7052 | |
| dc.identifier.issn | 1523-7060 | |
| dc.identifier.uri | https://hdl.handle.net/1721.1/128547 | |
| dc.description.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. | en_US |
| dc.description.sponsorship | National Institutes of Health (Grant R01-GM044783) | en_US |
| dc.description.sponsorship | National Science Foundation (Grant CHE-1764328) | en_US |
| dc.language.iso | en | |
| dc.publisher | American Chemical Society (ACS) | en_US |
| dc.relation.isversionof | http://dx.doi.org/10.1021/ACS.ORGLETT.9B03351 | en_US |
| dc.rights | Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use. | en_US |
| dc.source | PMC | en_US |
| dc.title | Hyperconjugative Antiaromaticity Activates 4 H -Pyrazoles as Inverse-Electron-Demand Diels–Alder Dienes | en_US |
| dc.type | Article | en_US |
| dc.identifier.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 | en_US |
| dc.contributor.department | Massachusetts Institute of Technology. Department of Chemistry | en_US |
| dc.relation.journal | Organic Letters | en_US |
| dc.eprint.version | Author's final manuscript | en_US |
| dc.type.uri | http://purl.org/eprint/type/JournalArticle | en_US |
| eprint.status | http://purl.org/eprint/status/PeerReviewed | en_US |
| dc.date.updated | 2020-11-19T17:45:41Z | |
| dspace.orderedauthors | Levandowski, BJ; Abularrage, NS; Houk, KN; Raines, RT | en_US |
| dspace.date.submission | 2020-11-19T17:45:44Z | |
| mit.journal.volume | 21 | en_US |
| mit.journal.issue | 20 | en_US |
| mit.license | PUBLISHER_POLICY | |
| mit.metadata.status | Complete | |
