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Updated: Aug 15, 2025

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Persistent azulene α-carbocations: synthesis from aldehydes, spectroscopic and crystallographic properties
Catajina Harabajiu1, Jodie L Hann1, Lloyd C Murfin1
1Department of Chemistry, University of Bath, Bath, BA2 7AY, UK. S.E.Lewis@bath.ac.uk.
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.
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