Asymmetric Induction in Liquid Crystals: Optically Active trans-Cyclooctene from Hofmann Elimination in New Cholesteric Mesophases

Article abstract of DOI:10.1021/jo01292a033

Optically active trans-cyclooctene was obtained by Hofmann elimination of trimethylcyclooctyl ammonium hydroxide in new cholesteric liquid crystals.The extent of asymmetric induction rose 7 percent.Enantiomeric equilibration of racemic trans-cyclooctene in cholesteric medium, at 180 deg C, leads to a 2 percent enantiomeric excess.These asymmetric induction results are interpreted in terms of solute-solvent interactions enhanced by the local ordering of the mesophase.