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 |
Section | 一般 |
Research Field |
Organic chemistry
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Research Institution | University of Tsukuba |
Principal Investigator |
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Project Period (FY) |
2011 – 2013
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Project Status |
Completed (Fiscal Year 2013)
|
Budget Amount *help |
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2013: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2012: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2011: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
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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 / 高歪みシグマ結合 / シグマ-パイ共役 / 反芳香族性 / Diels-Alder反応 / ケイ素置換基 / 高歪み分子 / 原子価異性化 / ケイ素 / 高歪みσ結合 / σ-π共役 / へテロ原子 |
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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Report
(4 results)
Research Products
(85 results)
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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
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