- Perfluoro allyl fluorosulfate (FAFS): A versatile building block for new fluoroallylic compounds
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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.
- Wlassics, Ivan,Tortelli, Vito,Carella, Serena,Monzani, Cristiano,Marchionni, Giuseppe
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scheme or table
p. 6512 - 6540
(2011/10/13)
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- Fluorosulfonation. Insertion of Sulfur Trioxide into Allylic C-F Bonds
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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.
- Krespan, Carl G.,Dixon, David A.
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p. 4460 - 4466
(2007/10/02)
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- β-Substituted polyfluoropropionate salts and derivatives
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β-substituted polyfluoropropionate salts, derivatives and copolymers and processes for the preparation thereof.
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- Perfluoroallyl fluorosulfate and its sultone and polymers
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Hexafluoropropene is reacted with liquid sulfur trioxide in the presence of boric oxide, boron trichloride, boron trifluoride, tri(lower alkyl) borate, boron trioxychloride or boron trioxyfluoride at from 0° C. to 150° C. to form perfluoroallyl fluorosulfate and the sultone thereof. The perfluoroallyl fluorosulfate can be homopolymerized or copolymerized with various fluoroethylenes to form resins useful as ion exchange resins or catalysts. The fluorosulfate groups on the resins can be hydrolyzed to form carboxylic acid groups or various corresponding salts. The sultone of perfluoroallyl fluorosulfate can be rearranged to form β-fluorocarbonyl-β-fluorosulfonyl-trifluorethyl fluorosulfate.
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