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Synthesis and Stereochemistry of New Bis(1,3-Oxathian-2-yl) Derivatives: Epimerisation and Chair–Twist Equilibria
Authors:C Cismaş  I Grosu  G Plé  E Condamine  Y Ramondenc  L Toupet  I Silaghi-Dumitrescu  G Nemeş  A Terec  L Muntean
Institution:(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
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.
Keywords:1  3-Oxathianes  epimerisation of diastereoisomers  X-ray structures  variable temperature NMR  ab-initio level calculations
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