Synthesis of α-trifluoromethylated amides by Eschenmoser–Claisen-type rearrangement of allylic alcohols

Walkowiak, Justyna B.; Tomas-Szwaczyk, Magdalena; Haufe, Günter; Koroniak, Henryk

doi:10.1016/j.jfluchem.2012.07.011

Cited by 10 publications

(5 citation statements)

References 58 publications

(16 reference statements)

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“…7) [41]. Similar reaction leading to the corresponding unsaturated fluorinated amides was also reported for the reaction of Ishikawa reagent [42] and [(C 2 H 5 ) 2 NCF = CHCF 3 , DEPFPA] [43] with allylic alcohols, as a result of Eschenmoser-Claisen-type rearrangement.…”

Section: Ohsupporting

confidence: 64%

Fluoroolefin-Amine Adduct Deoxofluorination

Петров¹

2017

Fluorination

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Section: Ohsupporting

confidence: 64%

Fluoroolefin-Amine Adduct Deoxofluorination

Петров¹

2017

Fluorination

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“…In the course of their study on the preparation of α-trifluoromethylated amides from allylic alcohols, Walkowiak and co-workers reported a case where 2-fluoroallyl alcohol was used (Scheme 19). 33 Upon reaction with 1,1,3,3,3-pentafluoroprop-1-ene-diethylamine adduct (PFPDEA), a 1,5-di-ene was formed, which then underwent an Eschenmoser-Claisen-type rearrangement to afford a monofluoroalkenebearing amide in modest yield.…”

Section: Pericyclic Reactionsmentioning

confidence: 99%

“…Walkowiak and co-workers synthesized various fluorinated allylic alcohols and studied their behavior in an Eschenmoser-Claisen type rearrangement. 33 Reaction of the 2-fluoroallyl alcohols with 1,1,3,3,3-pentafluoropropenediethylamine adduct gave fluoroalkene-containing α-(tri-…”

Section: Scheme 146 Overman Rearrangement Of 2-fluoroallyl Trichloroamentioning

confidence: 99%

Synthesis of Monofluoroalkenes: A Leap Forward

2018

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Monofluoroalkenes have found wide application in organic chemistry, medicinal chemistry, and materials science. This review summarizes the most recent advances made regarding the preparation of monofluoroalkenes, covering the period between October 2010 and September 2017. This review is divided in three main parts, one for each possible substitution pattern, namely di-, tri-, and tetrasubstituted. Then, for each class, further subclassification is made according to the reaction type.1 Introduction2 Disubstituted Monofluoroalkenes2.1 Disubstituted α-Monofluoroalkenes2.2 Disubstituted β-Monofluoroalkenes3 Trisubstituted Monofluoroalkenes4 Tetrasubstituted Monofluoroalkenes5 Conclusions

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“…[20] Several different variants of this type of rearrangement were applied for the synthesis of fluoroorganic compounds. [21] There are also examples of the use of Claisen rearrangement in the synthesis involving sugar molecules, both non-and fluorinated. [22] We report herein the synthesis of the fluorine-containing amides developed from a mannitol-based precursor by Claisen rearrangement.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Fluorinated Amides Starting from Carbohydrates Based on the Claisen Rearrangement

2022

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The search for new methods for installation of fluorine atoms into organic molecules is still a widely studied issue. In this work, an efficient synthetic protocol for 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 1H, 19F and 13C NMR spectroscopy and high resolution mass spectrometry. The X‐ray crystal structures of some fluorinated derivatives were obtained confirming structure, geometry and 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.

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Synthesis of α-trifluoromethylated amides by Eschenmoser–Claisen-type rearrangement of allylic alcohols

Cited by 10 publications

References 58 publications

Fluoroolefin-Amine Adduct Deoxofluorination

Fluoroolefin-Amine Adduct Deoxofluorination

Synthesis of Monofluoroalkenes: A Leap Forward

Synthesis of Fluorinated Amides Starting from Carbohydrates Based on the Claisen Rearrangement

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