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Enantiomerization of allylic trifluoromethyl sulfoxides studied by HPLC analysis and DFT calculations

Enantiomerization of allylic trifluoromethyl sulfoxides occurs spontaneously at room temperature through the corresponding allylic trifluoromethanesulfenates via a [2,3]-sigmatropic rearrangement. Dynamic enantioselective high-performance liquid chromatography (HPLC) analysis revealed the stereodyna...

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Main Authors: Bailly, Laetitia (Author) , Petit, Emilie (Author) , Maeno, Mayaka (Author) , Shibata, Norio (Author) , Trapp, Oliver (Author) , Cardinael, Pascal (Author) , Chataigner, Isabelle (Author) , Cahard, Dominique (Author)
Format: Article (Journal)
Language:English
Published: 2016
In: Chirality
Year: 2015, Volume: 28, Issue: 2, Pages: 136-142
ISSN:1520-636X
DOI:10.1002/chir.22552
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/chir.22552
Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chir.22552
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Author Notes:Laetitia Bailly, Emilie Petit, Mayaka Maeno, Norio Shibata, Oliver Trapp, Pascal Cardinael, Isabelle Chataigner, and Dominique Cahard
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Summary:Enantiomerization of allylic trifluoromethyl sulfoxides occurs spontaneously at room temperature through the corresponding allylic trifluoromethanesulfenates via a [2,3]-sigmatropic rearrangement. Dynamic enantioselective high-performance liquid chromatography (HPLC) analysis revealed the stereodynamics of these sulfoxides ranging from chromatographic resolution to peak coalescence at temperatures between 5 and 53 °C. The rate constant of enantiomerization and activation parameters were determined and compared with Density Functional Theory (DFT) calculations. Chirality 28:136-142, 2016. © 2015 Wiley Periodicals, Inc.
Item Description:Published online 21 December 2015
Gesehen am 19.08.2020
Physical Description:Online Resource
ISSN:1520-636X
DOI:10.1002/chir.22552

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