Synthesis and Stereochemistry of New Bis(1,3-Oxathian-2-yl) Derivatives: Epimerisation and Chair–Twist Equilibria |
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Authors: | C. Cismaş I. Grosu G. Plé E. Condamine Y. Ramondenc L. Toupet I. Silaghi-Dumitrescu G. Nemeş A. Terec L. Muntean |
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Affiliation: | (1) Faculty of Chemistry and Chemical Engineering, “Babes-Bolyai” University, 11 Arany Janos Street, 400028 Cluj-Napoca, Romania;(2) Faculté des Sciences, Université de Rouen et IRCOF, UMR A-6014, 76821 Mont Saint-Aignan Cedex, France;(3) Université de Rennes 1, UMR C-6626, Bat. 11A, Campus de Beaulieu, 35042 Rennes Cedex, France |
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Abstract: | The synthesis and stereochemistry of some new bis(1,3-oxathian-2-yl) derivatives are reported. The conformational behavior of these compounds and the orientation of their substituents are deduced from the NMR spectra, from the X-ray crystal structures of two compounds and from the ab-initio level calculations. The epimerization of diastereoisomers and the chair ⇌ 22,5-twist equilibria were studied by variable temperature NMR. |
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Keywords: | 1,3-Oxathianes epimerisation of diastereoisomers X-ray structures variable temperature NMR ab-initio level calculations |
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