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Monatshefte für Chemie / Chemical Monthly

, Volume 131, Issue 4, pp 345–352 | Cite as

Hydroacridines XXI [1]. 13C NMR Spectroscopic Investigation of the Stereoselectivities of Quaternizations of N-Alkyl Derivatives of (4aα,8aβ,9aβ,10aα)- and (4aα,8aα,9aβ,10aα)-Tetradecahydroacridine

  • Francisc Potmischil
  • Helmut Herzog
  • Joachim Buddrus
  • Mircea D. Gheorghiu

Summary.

 The stereoselectivities of the quaternization reactions of (4aα,8aβ,9aβ,10aα)- and (4aα,8aα,9aβ,10aα)-tetradecahydro-10-methylacridine with methyl- and ethyl iodide as well as those of (4aα,8aβ,9aβ,10aα)- and (4aα,8aα,9aβ,10aα)-10-ethyl-tetradecahydroacridine with methyl iodide were investigated using 13C NMR spectroscopy including 13C-labelling where appropriate. The methylations of both N-methyl amines occur by predominant (60% and 75%, respectively) equatorial approach, their ethylations occur sterospecifically by equatorial approach, and the methylations of the N-ethyl amines occur by highly stereoselective (> 90%) axial approach of the quaternizing reagent.

Keywords. Acridines, tetradecahydro; 13C NMR; 13C-Labelling; Stereoselective reactions. 

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Copyright information

© Springer-Verlag/Wien 2000

Authors and Affiliations

  • Francisc Potmischil
    • 1
  • Helmut Herzog
    • 2
  • Joachim Buddrus
    • 2
  • Mircea D. Gheorghiu
    • 3
  1. 1. Department of Organic Chemistry, University of Bucharest, RO-70031 Bucharest, RomaniaRO
  2. 2. Institut für Spektrochemie und Angewandte Spektroskopie, D-44139 Dortmund, GermanyDE
  3. 3. Department of Organic Chemistry, Politehnica University, RO-78126 Bucharest, RomaniaRO

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