Determination of the absolute stereochemistry and the activation barriers of thermally interconvertible heterocyclic compounds bearing a naphthyl substituent

  • Demir-Ordu Ö
  • Yilmaz E
  • Doǧan I
  • 3

    Readers

    Mendeley users who have this article in their library.
  • 16

    Citations

    Citations of this article.

Abstract

The enantiotopic methyl signals of the compounds studied were resolved in the presence of the optically active chiral auxiliary (S)-(+)-2,2,2- trifluoroanthryl ethanol, [(S)-TFAE] via complex formation between (S)-TFAE and the respective compounds. Two different solvation models were proposed for both M and P conformations leading to the assignments of the1H NMR signals and thus absolute conformations. The solvation models proposed also explained the strong temperature dependence of the1H NMR signals upon cooling. The activation barriers for interconversion between the enantiomers of the compounds studied have been determined by either temperature dependent NMR or enantioresolution on a chiral sorbent via HPLC. © 2005 Elsevier Ltd. All rights reserved.

Get free article suggestions today

Mendeley saves you time finding and organizing research

Sign up here
Already have an account ?Sign in

Find this document

Authors

  • Öznur Demir-Ordu

  • Esra Müjde Yilmaz

  • Ilknur Doǧan

Cite this document

Choose a citation style from the tabs below

Save time finding and organizing research with Mendeley

Sign up for free