Generalization of neighboring group participation onto non-carbon cation
| Project/Area Number |
15K14927
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| Research Category |
Grant-in-Aid for Challenging Exploratory Research
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| Allocation Type | Multi-year Fund |
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| Research Field |
Chemical pharmacy
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| Research Institution | The University of Tokyo |
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Principal Investigator |
Ohwada Tomohiko 東京大学, 大学院薬学系研究科(薬学部), 教授 (20177025)
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| Research Collaborator |
NING Yingtang
FUKUDA Tomoya
OTANI Yuko
IKEDA Hirotaka
KAWAHATA Masatoshi
YAMAGUCHI Kentaro
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| Project Period (FY) |
2015-04-01 – 2017-03-31
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| Project Status |
Completed (Fiscal Year 2016)
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| Budget Amount *help |
¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2016: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2015: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
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| Keywords | 隣接基関与 / 窒素カチオン / 転位反応 / タンデムな隣接基 / オキシム / Beckmann転位 |
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| Outline of Final Research Achievements |
Neighboring group participation is defined as the action of a substituent to stabilize a transition state or intermediate by forming a bond or partial bond to the reaction center. In addition to the primary interaction with the nearest neighboring group, secondary interactions involving another neighboring group(s) could also occur in principle. We revisited this issue by showing the influence of secondary interactions on the stability and reactivity of the putative iminylium cation intermediates, formed by N-O bond cleavage of 1-tetralone oxime systems. Direct observation of the peri-bromo-iminylium intermediate in solution supported the involvement of iminylium cations and the stabilizing effect of secondary interactions arising from a distal tandem substituent.
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Report
(3 results)
Research Products
(10 results)
