title: Perfluoro Allyl fluorosulfate (FAFS): a versatile building block for new fluoroallylic compounds.
abstract: In this study we will present and discuss both the synthesis of CF(2) = CFCF(2)OSO(2)F (perfluoroallyl fluorosulfate, FAFS), focusing in particular on the important role of C(3)F(6)/SO(3) ratio, reaction temperature and boron catalyst/SO(3) 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, H(2)O(2), 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 pK(a) 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.
authors.affiliation: Solvay Solexis, Viale Lombardia, 20-Bollate, Milan 20021, Italy. ivan.wlassics@solvay.com
authors.forename: Ivan
authors.initials: I
authors.lastname: Wlassics
authors.forename: Vito
authors.initials: V
authors.lastname: Tortelli
authors.forename: Serena
authors.initials: S
authors.lastname: Carella
authors.forename: Cristiano
authors.initials: C
authors.lastname: Monzani
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Marchionni
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000498:Allyl Compounds / Q000138:chemical synthesis*; D001895:Boron / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D004987:Ethers / Q000737:chemistry; D005459:Fluorides / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D006219:Halogens / Q000737:chemistry; D006861:Hydrogen Peroxide / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D007700:Kinetics; D013237:Stereoisomerism; D013464:Sulfuric Acids / Q000737:chemistry*
chemical_list: D000438:Alcohols; D000498:Allyl Compounds; D004987:Ethers; D005609:Free Radicals; D006219:Halogens; D007659:Ketones; D013464:Sulfuric Acids; D006861:Hydrogen Peroxide; D001895:Boron; C046106:fluorosulfonic acid; D005459:Fluorides