680-15-9 | Methyl 2,2-difluoro-2-(fluorosulfonyl)acetate

CAS:680-15-9 | Methyl 2,2-difluoro-2-(fluorosulfonyl)acetate ,Description

Methyl 2,2-difluoro-2-(fluorosulfonyl)acetate (DFSA) is an organofluoride compound with a variety of applications in the scientific research field. It is an important reagent for the synthesis of organic compounds, and its unique properties make it a valuable tool for laboratory experiments.
 

Scientific Research Applications

1. Source of Difluorocarbene

Methyl 2,2-difluoro-2-(fluorosulfonyl)acetate (MDFA) acts as an efficient source of difluorocarbene under high concentration and temperature conditions. It exhibits carbene reactivity characteristics similar to those of trimethylsilyl 2,2-difluoro-2-(fluorosulfonyl)acetate (TFDA), leading to high yields of difluorocyclopropane products in reactions with n-butyl acrylate (Eusterwiemann, Martínez, & Dolbier, 2012).

2. Synthesis of Difluoromethylene Triphenylphosphonium Ylide

In the presence of demethylating agents like iodide, MDFA releases difluorocarbene, which then forms difluoromethylene triphenylphosphonium ylide with triphenylphosphine. This facilitates a Wittig-type reaction with carbonyl reactants, producing 1,1-difluoroalkenes in good yield (Thomoson, Martínez, & Dolbier, 2013).

3. Reactivity with Silver Oxide and Carbonate

The reactivity of the sulfofluoride group in MDFA with silver oxide and carbonate is crucial for applications in advanced technologies like membrane and catalytic technologies. The synthesis of silver 2,2-difluoro-2(fluorosulfonyl)acetate was successfully performed using silver carbonate and carboxylic acid fluoride (Emel'yanov et al., 2011).

4. Role in Radical Reactions

MDFA is involved in radical reactions with vinyl ethers, leading to the synthesis of various difluoro or monofluoroacetyl-substituted acetals. This methodology has been applied in the synthesis of novel 3,3-difluoro-GABA compounds, expanding the range of isomeric difluoro GABAs (Kondratov et al., 2015).

5. Synthesis of Oxazolyl Sulfonyl Fluoride Warheads

MDFA plays a role in the synthesis of oxazolyl sulfonyl fluorides, demonstrating its utility in medicinal chemistry, chemical biology, and drug discovery. This process involves the Rh2(OAc)4-catalyzed annulation of MDFA with nitriles, providing a route to highly functionalized oxazolyl-decorated sulfonyl fluoride warheads (Fang et al., 2020).

6. Influence on Structure and Configurational Stability

MDFA, particularly its sulfonyl and fluorosulfonyl analogs, significantly influences the structure and stability of α-sulfonyl carbanions. This effect is critical in understanding the chemistry of these compounds and their applications in synthetic chemistry (Raabe, Gais, & Fleischhauer, 1996).

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