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Stabilization of a Strained Heteroradialene by Peripheral Electron Delocalization

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journal contribution
posted on 31.03.2016 by S. Hessam M. Mehr, Brian O. Patrick, Mark J. MacLachlan
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.