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Isomerization of Hydrofluorocyclopentenes Promoted by Fluoride Anion
Beijing Institute of Technology, Beijing, China
Beijing Institute of Technology, Beijing, China
Beijing Institute of Technology, Beijing, China
Beijing Institute of Technology, Beijing, China
National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Japan
- 1 Beijing Institute of Technology, Beijing, China
- 2 Beijing Institute of Technology, Beijing, China
- 3 Beijing Institute of Technology, Beijing, China
- 4 Beijing Institute of Technology, Beijing, China
- 5 National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba, Japan
Green and Sustainable Chemistry·Volume 08 (2017)·Pages 115–129·Published 28 December 2017·DOI10.4236/gsc.2018.81008
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Abstract
The isomerization of hydrofluorocyclopentenes promoted by fluoride anion was investigated. It was found that two processes were responsible for interconversion of the isomers: an allylic syn-addition/elimination of fluoride anion that does not change the mutual positions of hydrogen atoms but is responsible for transfers of fluorine atoms, and a fluoride anion-assisted deprotonation/protonation which does not change the mutual positions of fluorine atoms but is responsible for transfers of hydrogen atoms. In the deprotonation, HF can easily capture excess fluoride anion to form HF 2 - anion which can probably inhibit the protonation.
KeywordsHydrofluorocyclopenteneAllylic Syn-Addition/EliminationDeprotonation/Protonation
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