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Synthesis of Fluorinated Amides Starting from Carbohydrates Based on the Claisen Rearrangement
Authors:
- Monika Bilska-Markowska,
- Ewa Maria Patyk-Kaźmierczak,
- Aleksandra Lusina
- Record ID
- UAMe625d7f0b106424f88c6e4dfeaa446c7
- Author
- Journal series
- European Journal of Organic Chemistry, ISSN 1434-193X, e-ISSN 1099-0690, [1099-0690]
- Issue year
- 2022
- Vol
- 2022
- No
- 2
- Pages
- 1-6
- Article number
- e202101378
- ASJC Classification
- ;
- Abstract in original language
- The search for new methods for installation of fluorine atoms into organic molecules is still a widely studied issue. In this paper an efficient synthetic protocol towards the synthesis of fluorine-containing amides derived from sugar has been presented. This approach involved the Claisen rearrangement of previously obtained fluorinated vinyl ethers. The three fluorinated olefins: 1,1,3,3,3-pentafluoroprop-1-ene (2H-PFP), 1,2,3,3,3-pentafluoroprop-1-ene (1H-PFP) and hexafluoroprop-1-ene (HFP) were used as a source of fluorine. New compounds were characterized by 1 H, 19 F and 13 C NMR spectroscopy and high resolution mass spectrometry. The X-Ray crystal structures of some fluorinated derivatives were obtained confirming the structure, geometry and the absolute configuration. The resulting molecules, due to possibility of further transformation of their functional groups, can be valuable fluorinated scaffolds for the synthesis of subsequent chemical compounds
- DOI
- DOI:10.1002/ejoc.202101378 Opening in a new tab
- URL
- https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202101378 Opening in a new tab
- Language
- eng (en) English
- Score (nominal)
- 70
- Score source
- journalList
- Score
- = 70.0, 24-03-2022, ArticleFromJournal
- Publication indicators
- = 0; : 2018 = 0.626; : 2019 (2 years) = 2.889 - 2019 (5 years) =2.530
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- Uniform Resource Identifier
- https://researchportal.amu.edu.pl/info/article/UAMe625d7f0b106424f88c6e4dfeaa446c7/
- URN
urn:amu-prod:UAMe625d7f0b106424f88c6e4dfeaa446c7
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or PerishOpening in a new tab system.