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Updated: Mar 23, 2026

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Stabilization of a Strained Heteroradialene by Peripheral Electron Delocalization
S Hessam M Mehr1, Brian O Patrick1, Mark J MacLachlan1
1Department of Chemistry, University of British Columbia , 2036 Main Mall, Vancouver, BC V6T 1Z1, Canada.
Abstract:
Dimethylamine and 2,4,6-triformylphloroglucinol react to form a product with a highly contorted nonplanar geometry due to favorable electron delocalization. This new heteroradialene compound has been studied by X-ray diffraction, variable-temperature multinuclear NMR spectroscopy, IR spectroscopy, UV-vis spectroscopy, and ab initio calculations. Electron delocalization throughout the periphery of the central ring leads to a structure that retains very little of the aromatic characteristics of the starting material.
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