Stereodynamics and conformational chirality of the atropisomers of ditolyl anthrones and anthraquinone

J Org Chem. 2008 Jul 18;73(14):5354-9. doi: 10.1021/jo800677n. Epub 2008 Jun 21.

Abstract

Syn and anti conformers in similar proportions were observed at ambient temperature for the title compounds. The conformational assignment of the two anthrones was obtained by the observation of different multiplicity of the methylene NMR signals, whereas that of the anthraquinone derivative was determined by NOE experiments. The anti-to-syn interconversion barriers were obtained by line-shape simulation of the temperature-dependent NMR spectra, and by saturation transfer experiments. In one case the X-ray diffraction indicated that the syn is the only structure observed in the crystals.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthracenes / chemistry*
  • Crystallography, X-Ray
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Conformation
  • Stereoisomerism
  • Temperature

Substances

  • Anthracenes