773-15-9

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 82, p. 6181, 1960 DOI: 10.1021/ja01508a051

InChI:InChI=1/C3F6O3S/c4-1(2(5,6)7)3(8,9)12-13(1,10)11

Upstream product

• 116-15-4 perfluoropropylene 
• 7446-11-9 sulfur trioxide 

Downstream Products

• 3094-21-1 1,2,2,2-tetrafluoro-1-(methyl-phenyl-carbamoyl)-ethanesulfonyl fluoride 
• 18344-01-9 2,3,3,3-Tetrafluoro-2-fluorosulfonyl-propionic acid cyclohexyl ester 
• 754-41-6 2-(fluorosulfonyl)tetrafluoropropionyl fluoride 
• 132130-90-6 1-Benzyloxy-1,1,2,3,3,3-hexafluoro-propane-2-sulfonyl fluoride 
• 132130-94-0 1,1,1,2,3,3-Hexafluoro-3-pentafluorophenylmethoxy-propane-2-sulfonyl fluoride 
• 132130-92-8 1-(3,5-Bis-trifluoromethyl-benzyloxy)-1,1,2,3,3,3-hexafluoro-propane-2-sulfonyl fluoride 
• 116-15-4 perfluoropropylene 
• 201230-82-2 carbon monoxide 
• 7789-21-1 fluorosulphonic acid 
• 13002-01-2 chlorosulfuric acid pentafluoropropenyl ester 
• 65269-96-7 hexane-1-sulfonyl fluoride 
• 558-25-8 methyl fluorosulfonate 
• 7790-94-5 chlorosulfonic acid 

Relevant academic research and scientific papers

Perfluoro allyl fluorosulfate (FAFS): A versatile building block for new fluoroallylic compounds

In this study we will present and discuss both the synthesis of CF 2=CFCF2OSO2F (perfluoroallyl fluorosulfate, FAFS), focusing in particular on the important role of C3F 6/SO3 ratio, reaction temperature and boron catalyst/SO3 ratio on FAFS' yield and selectivity, as well as a wide variety of ionic and radical reactions possible with FAFS. We focused our attention on reactions of FAFS with aliphatic and aromatic alcohols, acyl halides, halides, H2O2, ketones and radicals whose synthesis and reaction mechanisms will be presented and discussed. Particular attention will be devoted to the novel diallyl-fluoroalkyl peroxide obtained. Factors such as pKa and Lowry and Pearson's Hard/Soft Acid-Base Theory which determine the selectivity between Addition/Elimination vs. Nucleophilic Substitution reaction mechanisms on FAFS will also be presented and discussed.

Perfluoroethanesulfonyl fluoride: Preparation from sultone

A procedure was developed for preparing perfluoroethanesulfonyl fluoride by synthesis of hexafluoropropane-2-β-sultone from sulfuric anhydride and perfluoropropene, followed by hydrolysis of the sultone to α- tetrafluoroethanesulfonyl fluoride and fluorination of the latter with elemental fluorine.

Fluorinated olefins and oleum

Oleum has some advantages over pure sulfur trioxide and may be successfully used for preparation of beta-sultones from hexafluoropropene, 2H-pentafluoropropene, 6H-perfluoro-1-hexene and perfluoro(propylvinyl) ether (VE). Depending on the reaction conditi

Fluorosulfonation. Insertion of Sulfur Trioxide into Allylic C-F Bonds

Insertion of sulfur trioxide into allylic C-F bonds of both terminal and internal fluoro olefins is shown to form the most stable olefinic products.A mechanism involving fluoroallyl cations as intermediates is proposed.State-of-the-art ab initio calculations of the ground-state energies for two isomeric unsaturated fluoro ethers establish the slightly greater stability (5.7 kcal/mol) of a vinyl ether over the corresponding fluoro olefin.A description of the optimized geometries of these molecules is also presented.

Preparation of perfluoroallyl fluorosulfate

Perfluoroallyl fluorosulfate is prepared by reacting hexafluoropropene with sulfur trioxide in the presence of boric oxide, boron trichloride, boron trifluoride tri(lower alkyl) borate, boron oxychloride or boron oxyfluoride.