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Persistent azulene α-carbocations: synthesis from aldehydes, spectroscopic and crystallographic properties.

Catajina HarabajiuJodie L HannLloyd C MurfinGabriele I Kociok-KöhnSimon E Lewis
Published in: Organic & biomolecular chemistry (2023)
The non-benzenoid aromatic system azulene is sufficiently nucleophilic at C1 that it can react with a protonated aldehyde to form an α-azulenyl alcohol. This in turn may be protonated and undergo loss of water to give an azulene α-carbocation. We report the isolation of such azulenyl cations as salts with non-coordinating anions. The salts have been characterised by NMR, UV/Vis absorption and (in certain cases) X-ray crystallography. Reduction of representative salts to afford azulenyl(aryl) methylenes has been demonstrated.
Keyphrases
  • ionic liquid
  • high resolution
  • magnetic resonance
  • molecular docking
  • cross sectional
  • fluorescent probe
  • sensitive detection
  • amino acid
  • solid state
  • mass spectrometry
  • molecular dynamics simulations