Preparation and Structural Study of the Enantiomers of α,α‘-Bis(trifluoromethyl)-9,10-anthracenedimethanol and Its Perdeuterated Isotopomer, Highly Effective Chiral Solvating Agents

Enantiopure forms of α,α‘-bis(trifluoromethyl)-9,10-anthracenedimethanol and the corresponding perdeuterated isotopomers were prepared. The conformational study was carried out by 1H NMR, and the absolute configuration was determined by the X-ray study of the crystallized diastereoisomeric carbamate...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-02, Vol.67 (3), p.753-758
Main Authors: Pomares, M., Sánchez-Ferrando, F., Virgili, A., Alvarez-Larena, A., Piniella, J. F.
Format: Article
Language:English
Subjects:
Chemistry
Condensed benzenic and aromatic compounds
Exact sciences and technology
Organic chemistry
Preparations and properties
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Summary:Enantiopure forms of α,α‘-bis(trifluoromethyl)-9,10-anthracenedimethanol and the corresponding perdeuterated isotopomers were prepared. The conformational study was carried out by 1H NMR, and the absolute configuration was determined by the X-ray study of the crystallized diastereoisomeric carbamate derivative. This compound was tested as a chiral solvating agent (CSA). The results showed very good discrimination for several racemic mixtures that improved other classical methods. The study of diastereomeric complexes was carried out by determination of the stoichiometry of the complex and the binding constant of the equilibrium.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo015957e