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Perfluoro Allyl Fluorosulfate (FAFS): A Versatile Building Block for New Fluoroallylic Compounds
Solvay Solexis, Viale Lombardia, 20-Bollate, Milan 20021, Italy
* Author to whom correspondence should be addressed.
Received: 27 June 2011; in revised form: 22 July 2011 / Accepted: 29 July 2011 / Published: 4 August 2011
Abstract: In this study we will present and discuss both the synthesis of CF2=CFCF2OSO2F (perfluoroallyl fluorosulfate, FAFS), focusing in particular on the important role of C3F6/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.
Keywords: perfluoroallyl fluorosulfate; addition/elimination reactions; fluorinated allyl ethers; perfluoro-diallyl peroxide; pKa
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Wlassics, I.; Tortelli, V.; Carella, S.; Monzani, C.; Marchionni, G. Perfluoro Allyl Fluorosulfate (FAFS): A Versatile Building Block for New Fluoroallylic Compounds. Molecules 2011, 16, 6512-6540.
Wlassics I, Tortelli V, Carella S, Monzani C, Marchionni G. Perfluoro Allyl Fluorosulfate (FAFS): A Versatile Building Block for New Fluoroallylic Compounds. Molecules. 2011; 16(8):6512-6540.
Wlassics, Ivan; Tortelli, Vito; Carella, Serena; Monzani, Cristiano; Marchionni, Giuseppe. 2011. "Perfluoro Allyl Fluorosulfate (FAFS): A Versatile Building Block for New Fluoroallylic Compounds." Molecules 16, no. 8: 6512-6540.