The aromaticity of the stannole dianion.
The aromaticity of the stannole dianion.
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DOI：
10.1002/anie.200501632
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发表时间：
2005-10
影响因子：
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通讯作者：
Masaichi Saito;Ryuta Haga;M. Yoshioka;K. Ishimura;S. Nagase
中科院分区：
文献类型：
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作者：
Masaichi Saito;Ryuta Haga;M. Yoshioka;K. Ishimura;S. Nagase
在过去的十年里，大量的注意力集中在硅杂环[1]和锗杂环[1f，2]的阴离子和二价阴离子上，它们是阴离子的重同系物。[3]甲硅烷基阴离子的芳香性程度取决于取代基[1b，f]，而锗烷基阴离子不显示芳香性，因为负电荷位于锗原子上。[1 f，2a，2c]相反，噻咯和锗摩尔的二价阴离子中的负电荷在C4M（M= Si，Ge）环中显著离域，并且它们被推断为芳香族的。[1d-f，2b，2d，2e，4]通过NMR研究、计算和X射线晶体结构分析证明了这些二价阴离子中的芳香离域，表明环内的C12C键没有变化。与siloles和germoles的一价和二价阴离子的研究相比，在我们几年前对这些物种进行研究之前，stannoles的一价和二价阴离子都没有报道。
In the last decade, much attention has been focused on the anions and dianions of siloles [1] and germoles,[1f, 2] which are heavier congeners of the cyclopentadienyl anion.[3] The degree of aromaticity of silolyl anions depends on the substituent,[1b, f] while the germolyl anions do not show aromaticity because the negative charge is localized on the germanium atom.[1 f, 2a, 2c] In contrast, the negative charges in the dianions of siloles and germoles are significantly delocalized in the C4M (M= Si, Ge) ring and they were concluded to be aromatic.[1d–f, 2b, 2d, 2e, 4] The aromatic delocalization in these dianions was evidenced by NMR studies, calculations, and X-ray crystal structural analyses, which showed no alternation of the CÀC bonds within the ring. In contrast to the wellinvestigated mono-and dianions of siloles and germoles, neither mono-nor dianions of stannoles had been reported before we undertook a study of such species a few years ago.