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

Catajina Harabajiu, Jodie L. Hann, Lloyd C. Murfin, Gabriele Kociok-Köhn, Simon E. Lewis

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Abstract

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.

Original languageEnglish
Pages (from-to)858-866
Number of pages9
JournalOrganic and Biomolecular Chemistry
Volume21
Issue number4
Early online date5 Jan 2023
DOIs
Publication statusPublished - 5 Jan 2023

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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