抗芳香性
环辛四烯
平面的
化学
表征(材料科学)
产量(工程)
部分
戒指(化学)
分子
计算化学
材料科学
立体化学
纳米技术
芳香性
有机化学
计算机科学
冶金
计算机图形学(图像)
作者
Thomas Hensel,Denis Trpcevski,Christopher Trier Lind,Rémi Grosjean,Peter Hammershøj,Christian Nielsen,Theis Brock‐Nannestad,Bjarne E. Nielsen,Magnus Schau‐Magnussen,B. F. Minaev,Gleb V. Baryshnikov,Michael Pittelkow
标识
DOI:10.1002/chem.201303194
摘要
Abstract In this paper we describe a new class of antiaromatic planar cyclooctatetraenes: the diazadioxa[8]circulenes. The synthesis was achieved by means of a new acid‐mediated oxidative dimerization of 3,6‐dihydroxycarbazoles to yield the diazadioxa[8]circulenes in high yields. The synthetic protocol appears to be general, and is a one‐pot transformation in which two CC bonds and two CO bonds are formed with the loss of two molecules of water. We also present a detailed characterization of the optical and electrochemical properties of this new class of stable planar cyclooctatetraenes. The properties of the diazadioxa[8]circulenes are compared with the properties of isoelectronic tetraoxa[8]circulenes and azatrioxa[8]circulenes. We discuss the antiaromatic nature of the planar central cyclooctatetraene moiety. The antiaromatic nature of the planar cyclooctatetraenes was studied by using computational methods (NICS calculations), and these calculations reveal that the central eight‐membered ring has antiaromatic character.
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