Stabilization of a Strained Heteroradialene by Peripheral Electron Delocalization

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.