2015 Fiscal Year Final Research Report
Development of Systematic Methods for Regioselective Syntheses of Fluorine-Substituted Polycyclic Aromatic Hydrocarbons
| Project/Area Number |
25288016
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Partial Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Organic chemistry
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| Research Institution | University of Tsukuba |
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Principal Investigator |
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| Project Period (FY) |
2013-04-01 – 2016-03-31
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| Keywords | フッ素 / 芳香族化合物 / 縮合環 / カチオン環化 / アルケン / アレン / 求電子的活性化 / 有機半導体 |
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| Outline of Final Research Achievements |
Three types of synthetic methods for the regioselectively fluorinated polycyclic aromatic hydrocarbons (F-PAHs) have been developed via Friedel-Crafts-type cyclizations by using electrophilic activation of fluoroalkenes with metal complexes or Lewis acids. When 1,1-difluoro-1-alkenes, 1,1,2-trifluoro-1-alkenes, 1,1-difluoroallenes, and 2-trifluoromethyl-1-alkenes were used as starting materials, the positions of C-C bond formation and fluorine introduction were perfectly controlled by α-cation stabilizing effect of fluorine substituents. Both of these synthetic methods for angular F-PAHs and linear F-PAHs are used in combination to fulfill our objective, systematic syntheses of regioselectively-fluorinated polycyclic aromatic hydrocarbons.
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| Free Research Field |
有機化学
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