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 2OSO 2F (perfluoroallyl fluorosulfate, FAFS), focusing in particular on the important role of C 3F 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 2O 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 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.