Persistent azulene α-carbocations: synthesis from aldehydes, spectroscopic and crystallographic properties?
Organic & Biomolecular Chemistry Pub Date: 2023-01-05 DOI: 10.1039/D2OB01695H
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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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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