Synthetic Studies of Silyne with Silicon-Carbon Triple Bond
Project/Area Number |
26620051
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Research Category |
Grant-in-Aid for Challenging Exploratory Research
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Allocation Type | Multi-year Fund |
Research Field |
Inorganic chemistry
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Research Institution | Kindai University |
Principal Investigator |
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Project Period (FY) |
2014-04-01 – 2017-03-31
|
Project Status |
Completed (Fiscal Year 2016)
|
Budget Amount *help |
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2016: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2015: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2014: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
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Keywords | silyne / silicon / triple bond / synthetic studies / diazomethane / disilyne / carbene / bulky substituent / シリン / ケイ素 / 三重結合 / 合成化学 / ジアゾメタン / ジシリン / カルベン / 立体保護基 / N-へテロ環状カルベン / ブロモシリレン / N-ヘテロ環状カルベン |
Outline of Final Research Achievements |
In this study, we challenged the synthesis of "silyne" having Si-C triple bond. We examined the reaction of the bulky Rind-substituted dibrormodisilenes, (Rind)BrSi=SiBr(Rind) (Rind = 1,1,3,3,5,5,7-octa-R-substituted s-hydrindacen-4-yl), with N-heterocyclic carbenes (NHCs), producing the bromosilylene-NHC adducts. We also performed the synthesis and characterization of a thermally stable "half-parent" type of diazomethane, (Rind)CHN2, whose structure was determined by X-ray crystallography. The photolysis of (Rind)CHN2 afforded a mixture of the expected cyclic product via the C-H insertion reaction of the generated triplet carbene species and the unexpected nitrile compound, (Rind)CN, as a minor product. We examined the reaction of (Rind)CHN2 with n-butyl lithium (n-BuLi) to produce (Rind)CHN2-n-BuLi adduct, which was confirmed by X-ray diffraction analysis. We also performed the synthetic studies of disilyne with Si-Si triple bond employing the extremely bulky MPind groups.
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Report
(4 results)
Research Products
(24 results)