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Monosubstituted 3,3‐Difluorocyclopropenes as Bench‐Stable Reagents: Scope and Limitations.
- Source :
- European Journal of Organic Chemistry; 12/21/2021, Vol. 2021 Issue 47, p6604-6615, 12p
- Publication Year :
- 2021
-
Abstract
- A general approach to gem‐difluorocyclopropenes synthesis based on the reaction of alkynes with Ruppert‐Prakash reagent is reported. The proposed method is evaluated for the synthesis of a wide difluorocyclopropenes scope based on their bench lifespan and hydrolytic stability. The tolerance of the method for common functional groups was shown. Previously unavailable difluorocyclopropenes substituted with aliphatic were prepared using the proposed procedure. The retain of stability was proven by the multigram scale synthesis and further storage in the temperature interval −78 to −4 °C over a year. This makes them attractive building blocks and intermediates for organic synthesis. The reasons for dropping stability were defined. The relations between the structure of the substituents and the stability of the difluorocyclopropene ring were determined and discussed. [ABSTRACT FROM AUTHOR]
- Subjects :
- ORGANIC synthesis
STRUCTURAL stability
FUNCTIONAL groups
ALKYNES
BENCHES
Subjects
Details
- Language :
- English
- ISSN :
- 1434193X
- Volume :
- 2021
- Issue :
- 47
- Database :
- Complementary Index
- Journal :
- European Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 154273402
- Full Text :
- https://doi.org/10.1002/ejoc.202100921