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Published on: January 19, 2016
Perfluoro Allyl fluorosulfate (FAFS): a versatile building block for new fluoroallylic compounds
Ivan Wlassics1, Vito Tortelli, Serena Carella
1Solvay Solexis, Viale Lombardia, 20-Bollate, Milan 20021, Italy. ivan.wlassics@solvay.com
This research details the synthesis of perfluoroallyl fluorosulfate (FAFS) and explores its diverse ionic and radical reactions. Key factors influencing FAFS yield and selectivity were identified, alongside novel reaction pathways.
Area of Science:
- Organic Chemistry
- Fluorine Chemistry
- Reaction Mechanisms
Background:
- Perfluoroallyl fluorosulfate (FAFS) is a versatile fluorinated compound.
- Understanding its synthesis and reactivity is crucial for developing new fluorinated materials and reactions.
Purpose of the Study:
- To present the synthesis of FAFS, optimizing yield and selectivity.
- To explore a wide range of ionic and radical reactions involving FAFS.
- To elucidate reaction mechanisms, including factors influencing selectivity.
Main Methods:
- Investigated the impact of C(3)F(6)/SO(3) ratio, temperature, and catalyst on FAFS synthesis.
- Examined reactions of FAFS with various nucleophiles (alcohols, halides, H(2)O(2), ketones) and radicals.
- Applied pK(a) and Hard/Soft Acid-Base Theory to analyze reaction selectivity.
Main Results:
- Optimized conditions for FAFS synthesis were identified.
- A variety of novel ionic and radical reactions of FAFS were demonstrated.
- A new diallyl-fluoroalkyl peroxide was synthesized and characterized.
- Selectivity between addition/elimination and nucleophilic substitution was explained.
Conclusions:
- FAFS is a valuable synthon for diverse chemical transformations.
- Reaction conditions significantly influence FAFS synthesis outcomes.
- Understanding acid-base properties aids in predicting FAFS reactivity and selectivity.
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