Electrochemical Fluorination of Partially Fluorinated Dialkylethers. Synthesis of Sevoflurane Derivatives (CF3)2CHOCHF2, (CF3)2CHOCF3, and (CF3)2CFOCF3
- 1Julius Maximilian University Würzburg, Institute of Inorganic Chemistry, Institute for Sustainable Chemistry & Catalysis with Boron (ICB) Würzburg Germany
- 2Merck Electronics KGaA Darmstadt Germany
Abstract
Electrochemical fluorination in anhydrous hydrogen fluoride (ECF in aHF) according to the Simons process was used for the fluorination of the anesthetic sevoflurane (CF3)2CHOCH2F to yield (CF3)2CHOCHF2, (CF3)2CHOCF3, and (CF3)2CFOCF3. The related ethers RFOCH3 (RF = nC3F7, a mixture of nC4F9/iC4F9, iC4F9, tC4F9) were fluorinated to result in the respective mono‐, di‐, and trifluoromethyl ethers. The vapor pressure curves of selected fluorinated ethers, including (CF3)2CHOCHF2, (CF3)2CHOCF3, and (CF3)2CFOCF3, were determined, and the Antoine fit parameters were used for the extrapolation of the normal boiling points and the enthalpies of vaporization. In addition, the crystal structures of sevoflurane, (CF3)2CHOCH3, (CF3)2CHOCHF2, (CF3)2CHOCF3, and (CF3)2CFOCF3 were determined by x‐ray diffraction, providing a detailed insight into trends of the bond parameters and the intermolecular interactions in the solid state. The interpretation of the bond parameters is supported by calculated values (density functional theory, DFT).
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BibTeX
@article{knuplez2026electrochemical,
title = {{Electrochemical Fluorination of Partially Fluorinated Dialkylethers. Synthesis of Sevoflurane Derivatives (CF3)2CHOCHF2, (CF3)2CHOCF3, and (CF3)2CFOCF3}},
author = {Tanja Knuplez and Leon N. Schneider and Erik R. Csapo and Peer Kirsch and Nikolai V. Ignat'ev and Maik Finze},
journal = {Chemistry (Weinheim an Der Bergstrasse, Germany)},
year = {2026},
month = aug,
doi = {10.1002/chem.71589},
url = {https://doi.org/10.1002/chem.71589},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - Electrochemical Fluorination of Partially Fluorinated Dialkylethers. Synthesis of Sevoflurane Derivatives (CF3)2CHOCHF2, (CF3)2CHOCF3, and (CF3)2CFOCF3
AU - Tanja Knuplez
AU - Leon N. Schneider
AU - Erik R. Csapo
AU - Peer Kirsch
AU - Nikolai V. Ignat'ev
AU - Maik Finze
PY - 2026
DA - 2026/08/19
JO - Chemistry (Weinheim an Der Bergstrasse, Germany)
DO - 10.1002/chem.71589
UR - https://doi.org/10.1002/chem.71589
AB - Electrochemical fluorination in anhydrous hydrogen fluoride (ECF in aHF) according to the Simons process was used for the fluorination of the anesthetic sevoflurane (CF3)2CHOCH2F to yield (CF3)2CHOCHF2, (CF3)2CHOCF3, and (CF3)2CFOCF3. The related ethers RFOCH3 (RF = nC3F7, a mixture of nC4F9/iC4F9, iC4F9, tC4F9) were fluorinated to result in the respective mono‐, di‐, and trifluoromethyl ethers. The vapor pressure curves of selected fluorinated ethers, including (CF3)2CHOCHF2, (CF3)2CHOCF3, and (CF3)2CFOCF3, were determined, and the Antoine fit parameters were used for the extrapolation of the normal boiling points and the enthalpies of vaporization. In addition, the crystal structures of sevoflurane, (CF3)2CHOCH3, (CF3)2CHOCHF2, (CF3)2CHOCF3, and (CF3)2CFOCF3 were determined by x‐ray diffraction, providing a detailed insight into trends of the bond parameters and the intermolecular interactions in the solid state. The interpretation of the bond parameters is supported by calculated values (density functional theory, DFT).
SN - 0947-6539
SN - 1521-3765
ER -