Stabilization of a Strained Heteroradialene by Peripheral Electron Delocalization
journal contributionposted on 31.03.2016 by S. Hessam M. Mehr, Brian O. Patrick, Mark J. MacLachlan
Any type of content formally published in an academic journal, usually following a peer-review process.
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.