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• Wlassics, I
• Tortelli, V
• Carella, S
• Monzani, C
• Marchionni, G
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• Wlassics, I
• Tortelli, V
• Carella, S
• Monzani, C
• Marchionni, G
• [+] on PubMed
• Wlassics, I
• Tortelli, V
• Carella, S
• Monzani, C
• Marchionni, G

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Molecules 2011, 16(8), 6512-6540; doi:10.3390/molecules16086512

Article

Perfluoro Allyl Fluorosulfate (FAFS): A Versatile Building Block for New Fluoroallylic Compounds

Ivan Wlassics* , Vito Tortelli, Serena Carella, Cristiano Monzani and Giuseppe Marchionni

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

(This article belongs to the Special Issue Fluorine Chemistry)

Download PDF Full-Text [932 KB, uploaded 4 August 2011 17:46 CEST]

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 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.

Keywords: perfluoroallyl fluorosulfate; addition/elimination reactions; fluorinated allyl ethers; perfluoro-diallyl peroxide; pK_a

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