Next Article in Journal
Rauniticine-allo-Oxindole B and Rauniticinic-allo Acid B, New Heteroyohimbine-Type Oxindole Alkaloids from the Stems of Malaysian Uncaria longiflora var. pteropoda
Next Article in Special Issue
t-Bu2SiF-Derivatized D2-Receptor Ligands: The First SiFA-Containing Small Molecule Radiotracers for Target-Specific PET-Imaging
Previous Article in Journal
1,1’-(3-Methyl-4-phenylthieno[2,3-b]thiophene-2,5-diyl)diethanone as a Building Block in Heterocyclic Synthesis. Novel Synthesis of Some Pyrazole and Pyrimidine Derivatives
Previous Article in Special Issue
Recent Advances in the Application of SelectfluorTMF-TEDA-BF4 as a Versatile Mediator or Catalyst in Organic Synthesis
Molecules 2011, 16(8), 6512-6540; doi:10.3390/molecules16086512
Article

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

* ,
,
,
 and
Received: 27 June 2011 / Revised: 22 July 2011 / Accepted: 29 July 2011 / Published: 4 August 2011
(This article belongs to the Special Issue Fluorine Chemistry)
Download PDF [932 KB, uploaded 18 June 2014]

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 perfluoroallyl fluorosulfate; addition/elimination reactions; fluorinated allyl ethers; perfluoro-diallyl peroxide; pKa
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote
MDPI and ACS Style

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.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

Cited By

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert