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Systematic Studies on the Synthesis, Structures, and Properties of Aromatic Compounds Containing Heavier Group 14 Elements

含重14族芳香族化合物的合成、结构与性能的系统研究

基本信息

批准号：
11304045
负责人：
TOKITOH Norihiro
金额：
$ 24.65万
依托单位：
Kyoto University (2000-2001)Kyushu University (1999)
依托单位国家：
日本
项目类别：
Grant-in-Aid for Scientific Research (A)
财政年份：
1999
资助国家：
日本
起止时间：
1999 至 2001
项目状态：
已结题

项目摘要

There has been no stable, neutral heteraaromatic compounds containing heavier group 14 elements, and their structures and properties have been revealed yet. In this Project, we studied on the synthesis of new type of heteraaromatic compounds containing a heavier group 14 element by taking advantage of an effective steric protection group, 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl (Tbt), which is developed by us, and elucidated their structures and properties. Based on these results, we estimated the aromaticity of these compounds, systematically.We succeeded in the synthesis and isolation of the first stable silabenzene, 1-silanaphthalene, 2-silanaphthalene, 9-silaanthracene, germabenzene, and 2-germanaphthalene as stable crystals by taking advantage of Tbt group. The X-ray structural analyses, spectral data on NMR, UV/vis, and Raman spectroscopy, and theoretical calculations indicated that all these compounds are aromatic compounds as aromaticity these compounds showed the high reactivities to H_2O, alcohols, olefins, alkynes, ketones, and nitrile oxides and underwent ready addition of these reagents to the Si=C or Ge=C double-bond.We think that the new knowledge obtained in this project lays the foundations of the chemistry of heteraaromatic compounds containing heavier group 14 elements. We expect that novel properties and functions of heteraaromatic compounds containing heavier group 14 elements will be revealed on the basis of these results, showing the potential applicability and these chemistry will be applied to the synthesis of novel functional compounds and novel catalysis.

迄今为止，还没有发现稳定的、中性的含重14族元素的杂芳族化合物，其结构和性质也尚未完全揭示。本课题利用我们开发的一种有效的空间位阻保护基团2，4，6-三[双（三甲基硅基）甲基]苯基（Tbt），合成了新型的含重14族元素的杂芳环化合物，并对其结构和性质进行了表征。在此基础上，我们系统地估算了这些化合物的芳香性，并利用Tbt基团成功地合成和分离了第一个稳定的硅杂苯、1-硅杂萘、2-硅杂萘、9-硅杂蒽、锗杂苯和2-锗杂萘晶体。通过X-射线衍射、核磁共振、紫外可见光谱和拉曼光谱的分析和理论计算，证明这些化合物都是芳香族化合物，它们对水、醇、烯烃、炔、酮、和腈氧化物，并经历了这些试剂容易添加到Si=C或Ge=C双-我们认为，在这个项目中获得的新知识奠定了含重14族元素的杂芳族化合物的化学基础。我们期望在这些结果的基础上揭示含重14族元素的杂芳化合物的新性质和功能，显示潜在的应用性，并将这些化学应用于新型功能化合物的合成和新型催化。