Epimerization of trans‐Cycloalkenes with the X−C=C−SeR*‐Unit – The Steric Demand of X=H, F, Cl, Br, I, Me, Et and CF3
Helmut Poleschner,
Matthias Heydenreich,
Andreas J. Achazi
Abstract:Trans‐cycloalkenes with the X–C=C–SeR*‐unit and ring sizes from 9 to 20 have been synthesized. Bond the selenium atom is the chiral (S)‐o‐(1‐Methoxypropyl)phenyl‐residue R*, and X = H, F, Cl, Br, I, Me, Et and CF3. The planar‐chiral trans‐cycloalkenes in combination with the chiral residue R* exist as two diastereomers. These can be distinguished in principle by NMR spectroscopy. We have studied the epimerization of the trans‐cycloalkenes, i.e., the 180° rotation of the X–C=C‐unit through the cavity of the rin… Show more
Set email alert for when this publication receives citations?
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.