2022 Fiscal Year Final Research Report
Development of Novel Modification Method of Pyridine Framework Using Non-Electronic Activation
| Project/Area Number |
20K05498
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Review Section |
Basic Section 33020:Synthetic organic chemistry-related
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| Research Institution | Kochi University of Technology |
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Principal Investigator |
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| Project Period (FY) |
2020-04-01 – 2023-03-31
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| Keywords | 置換基間反発 / キノリン環 / ナフタレン / 非対称化 / 芳香族性 / 環歪み |
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| Outline of Final Research Achievements |
The non-electronic activation of aromatic compounds by steric repulsion between peri-substituents. 1-Methylquinolinium salts with an alkyl group substituted at the 8-position were synthesized, and it was confirmed that the quinoline framework is distorted as the 8-alkyl group became bulkier by theoretical and experimental approaches. It was also found that the reactivity increases with increasing the bulk of the 8-alkyl group.
The similar study was also carried out for naphthalenes substituted with halogen atoms at the 1- and 8-positions. It was found that the skeleton is distorted by steric repulsion between halogens, and that reactions such as halogen dance and homo coupling proceed.
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| Free Research Field |
有機合成化学
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| Academic Significance and Societal Importance of the Research Achievements |
芳香族化合物は材料科学など多くの分野で幅広く用いられているが、その骨格修飾法は意外と少なく、いくつかの反応様式に分類されている。本研究では置換基間反発により、芳香環の活性化を達成しており、新たな方法論を提供したという点でその意義は大きい。置換基が嵩高くなるにつれて、骨格の歪みが大きくなり、それに伴って反応性が向上することを系統的な検討により明らかにした。こうして得られた知見は当該分野の研究者にとって有用な情報になる。また、対称なナフタレン骨格を簡便な操作で非対称化することができ、従来法では入手が困難であった骨格が容易に得られることから合成化学的な有用性も高い。
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