Stabilization of a Strained Heteroradialene by Peripheral Electron Delocalization

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• 作者：S. Hessam M. Mehr ; Brian O. Patrick ; Mark J. MacLachlan
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：April 15, 2016
• 年：2016
• 卷：18
• 期：8
• 页码：1840-1843
• 全文大小：312K
• 年卷期：0
• ISSN：1523-7052

文摘

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.