Monatshefte für Chemie / Chemical Monthly

, Volume 107, Issue 4, pp 907–919 | Cite as

Beiträge zur Chemie der Pyrrolpigmente, 14. Mitt. Interkonversionsprozesse bei Arylmethylidenpyrrolinonen; ein Spezialfall atropisomerer, sterisch gehinderter Styrole

  • Heinz Falk
  • Otmar Hofer
  • Alfred Leodolter
Organische Chemie und Biochemie

On the chemistry of pyrrole pigments, XIV.: Interconversion processes of arylmethylidenepyrrolinones—a special case of atropisomerism in sterically hindered styrenes


Starting from a chiral substituted benzaldehyde diastereomeric arylmethylidenepyrrolinones were accessible. The geometrical structures of the corresponding isomers were investigated by lanthanide ion induced shift technique and UV spectroscopy. By equilibration studies, D-NMR measurements and kinetic data a complete picture of the various ground state enthalpy differences as well as the activation energies of the transition paths was gained.

The results are in accord with the barriers determined for two simple model derivatives belonging to the class of atropisomeric sterically hindered styrenes.


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Copyright information

© Springer-Verlag 1976

Authors and Affiliations

  • Heinz Falk
    • 1
  • Otmar Hofer
    • 1
  • Alfred Leodolter
    • 1
  1. 1.Organisch-chemisches InstitutUniversität WienWienÖsterreich

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