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首页> 外文期刊>Chemistry: A European journal >Azatrioxa[8]circulenes: Planar anti-aromatic cyclooctatetraenes
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Azatrioxa[8]circulenes: Planar anti-aromatic cyclooctatetraenes

机译：Azatrioxa [8] circulenes：平面抗芳族环辛酸酯

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摘要

We describe herein the first synthesis of a new class of anti-aromatic planar cyclooctatetraenes: the azatrioxa[8]circulenes. This was achieved by treating a suitably functionalised 3,6-dihydroxycarbazole with 1,4-benzoquinones or a 1,4-naphthoquinone. We fully characterised the azatrioxa[8]circulenes by using optical, electrochemical and computational techniques as well as by single-crystal X-ray crystallography. The results of a computational study (NICS) suggest that the central planar cyclooctatetraene is anti-aromatic when the molecules are in neutral or oxidised states (2+), and that the corresponding dianions are aromatic. We discuss the aromatic/anti-aromatic nature of the planar cyclooctatetraenes and compare them with the isoelectronic tetraoxa[8]circulenes. Planar cyclooctatetraenes: The first synthesis of a new class of anti-aromatic planar cyclooctatetraenes is described: the azatrioxa[8]circulenes (see scheme). The azatrioxa[8]circulenes were fully characterised by using optical, electrochemical and computational techniques as well as by single-crystal X-ray crystallography. The aromatic/anti-aromatic nature of the planar cyclooctatetraenes is discussed and compared with the isoelectronic tetraoxa[8]circulenes.
机译：我们在这里描述了新的一类抗芳族平面环辛酸酯的合成：氮杂三恶[8]环。这通过用1，4-苯醌或1，4-萘醌处理适当官能化的3，6-二羟基咔唑来实现。我们通过使用光学，电化学和计算技术以及单晶X射线晶体学来充分表征azatrioxa [8] circulenes。计算研究（NICS）的结果表明，当分子处于中性或氧化态（2+）时，中心平面的环辛八烯是抗芳族化合物，相应的二价阴离子是芳族化合物。我们讨论了平面环辛酸酯的芳香/抗芳香性质，并将其与等电子四氧杂[8] circulenes进行比较。平面环辛酸酯：新型抗芳族平面环辛酸酯的第一类合成物是：azatrioxa [8] circulenes（参见方案）。通过使用光学，电化学和计算技术以及单晶X射线晶体学，可以完全表征氮杂三恶[8]环。讨论了平面环辛酸酯的芳香/反芳香性质，并将其与等电子四氧杂[8]环进行了比较。

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