Tricyclic Quaternary Ammonium Salts Derived from Cinchona Alkaloids.

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  • Additional Information
    • Source:
      Publisher: American Chemical Society Country of Publication: United States NLM ID: 2985193R Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-6904 (Electronic) Linking ISSN: 00223263 NLM ISO Abbreviation: J Org Chem Subsets: MEDLINE
    • Publication Information:
      Publication: Columbus Oh : American Chemical Society
      Original Publication: Easton, Pa. [etc.]
    • Subject Terms:
      Cinchona Alkaloids/*chemistry ; Quaternary Ammonium Compounds/*chemistry; Carbon-13 Magnetic Resonance Spectroscopy ; Molecular Structure ; Proton Magnetic Resonance Spectroscopy ; Salts/chemistry ; Spectrometry, Mass, Electrospray Ionization ; Thermodynamics
    • Abstract:
      Tricyclic systems with quaternary bridgehead nitrogen atoms are rare but an interesting class of compounds. Chiral quinuclidine derivative salts with fused five and six-membered rings (X-ray) were obtained via modification of Cinchona alkaloids. The ease of ring formation was dependent on its size, while even mild activation sufficed to close the five membered ring. On the other hand the systems with fused benzene and a six-membered ring formed atropisomers separated by a barrier of ca. 15 kcal/mol, whose interconversion was studied by DFT and NMR.
    • Accession Number:
      0 (Cinchona Alkaloids)
      0 (Quaternary Ammonium Compounds)
      0 (Salts)
    • Publication Date:
      Date Created: 20161217 Date Completed: 20180530 Latest Revision: 20241210
    • Publication Date:
      20241210
    • Accession Number:
      10.1021/acs.joc.6b02348
    • Accession Number:
      27978749