2013 Fiscal Year Final Research Report
Tetrahedrane and Cyclobutadiene: Synthesis and Structure of Highly Strained Hydrocarbons
| Project/Area Number |
23550042
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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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| 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) |
2011 – 2013
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| Keywords | 高歪み化合物 / ケイ素化合物 / テトラヘドラン / シクロブタジエン / シグマーパイ共役 / 光誘起異性化 |
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| Research Abstract |
Tetrahedrane is a hydrocarbon with highly strained C-C sigma bonds. Because of the extremely strained skeleton, the increase in the energy level of C-C sigma-bond orbitals results in the sigma-pi conjugation. Cyclobutadiene is one of valence isomers of tetrahedrane and a cyclic unsaturated compound with four pi-electrons within a rectangular planar four-membered ring.
We have investigated the synthesis, structural analysis and properties of substituted tetrahedranes stabilized by silyl groups. The perfluoroaryl substituted cyclobutadiene derivatives were prepared as air- and moisture-sensitive red solids by the photochemical isomerization of the corresponding tetrahedranes. The first aryl substituted cyclobutadienes were characterized by spectroscopic data as well as by Xray crystallography. We also developed new versatile synthetic routes of substituted tetrahedranes, and reported more than 20 stable derivatives up to now.
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[Presentation] Boryl Substituted Tetrahedranes2012
Author(s)
Y. Inagaki, Y. Kobayashi, T. Ochiai, M. Nishina, M.Tanaka, M. Nakamoto, A. Sekiguchi
Organizer
3rd International Symposium on Creation of Functional Materials
Place of Presentation
University of Tsukuba, Tsukuba
Year and Date
20121210-11
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