Abstract
Abstract The insight into s-cis vs. s-trans conformational equilibria in simple activated olefins is of prime importance for transition state modeling and for understanding of stereo-chemical results of the reactions involving such olefins. Some acrylates and vinyl sulfoxides have been found recently to choose the corresponding s-cis conformation as the reactive conformation in their thermal cycloaddition and conjugate addition reactions. In the course of our ste-reochemical studies involving chiral phosphine oxides we were prompted to address analogous conformational issue in regard to the conjugated vinyl-phosphoryl moiety. The two P-epimeric vinyl phosphine oxides and served us as the model compounds and their detailed analysis in solution and in the solid state will be presented. The presentation will include 2D 1H NMR as well as the solid state and solution 13C NMR data, the X-ray and IR analysis and also, comparison with some reference compounds. The significance of the depicted s-cis conformations as well as of the syn-coplanar array of the P=O and C=O dipoles in the studied compounds is implied.
Published Version
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