Vinyllithium
Identifiers | |
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CAS Number |
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3D model (JSmol) |
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Beilstein Reference | 3587231 |
ChEBI |
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ChemSpider |
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ECHA InfoCard | 100.011.844 |
EC Number |
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Gmelin Reference | 723 |
PubChem CID |
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CompTox Dashboard (EPA) |
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InChI
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Properties | |
Chemical formula | C2H3Li |
Molar mass | 33.99 g·mol−1 |
Appearance | white solid |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards | pyrophoric |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references |
Vinyllithium is an organolithium compound with the formula LiC2H3. A colorless or white solid, it is encountered mainly as a solution in tetrahydrofuran (THF). It is a reagent in synthesis of organic compounds, especially for vinylations.[1]
Preparation and structure
Solutions of vinyllithium are prepared by lithium-halogen exchange reactions. A halide-free route entails reaction of tetravinyltin with butyllithium:
- Sn(CH=CH2)4 + 4 BuLi → SnBu4 + 4 LiCH=CH2
The reaction of ethylene and lithium affords vinyl lithium and lithium hydride, together with other organolithium compounds,[1]
Like most organolithium compounds, vinyllithium crystallizes from THF as a cluster compound as a cubane-type cluster.[2]
Reactions
Vinyllithium is used to install vinyl groups on metal-based reagents, i.e., vinylations. It is a precursor to vinylsilanes, vinylcuprates, and vinylstannanes.[3] It adds to ketones compounds to give allylic alcohols. Vinylmagnesium bromide is often used in place of vinyllithium.[4]
Alternative reagents
Vinyl magnesium bromide, a Grignard reagent, is in many ways easier to generate in the laboratory and behaves similarly to vinyllithium.[5]
References
- ^ a b Eisenhart, Eric K.; Bessieres, Bernard (2007). "Vinyllithium". E-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rv015.pub2. ISBN 978-0-471-93623-7..
- ^ Walter Bauer; Frank Hampel (1992). "X-Ray crystal structure of a vinyllithium–tetrahydrofuran solvate (C2H3Li–thf)4. Quantitative estimation of Li–H distances by 6Li–1H HOESY". J. Chem. Soc., Chem. Commun. (12): 903–905. doi:10.1039/C39920000903.
- ^ Lipshutz, Bruce H.; Moretti, Robert; Crow, Robert (1990). "Mixed Higher-order Cyanocuprate-induced Epoxide Openings: 1-benzyloxy-4-penten-2-ol". Org. Synth. 69: 80. doi:10.15227/orgsyn.069.0080.
- ^ Dietmar Seyferth (1959). "Di-n-butyldivinyltin". Org. Synth. 39: 10. doi:10.15227/orgsyn.039.0010.
- ^ William J. Scott, G. T. Crisp, J. K. Stille (1990). "Palladium-catalyzed Coupling of Vinyl Triflates with Organostannanes: 4-tert-Butyl-1-Vinylcyclohexene and 1-(4-tert-Butylcyclohexen-1-yl)-2-propen-1-one". Organic Syntheses. 68: 116. doi:10.15227/orgsyn.068.0116.
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- LiF4Al
- Li3F6Al
- FLiBe
- LiFePO4
- FLiNaK
- LiGaH4
- Li2GeF6
- Li2GeO3
- LiGe2(PO4)3
- LiH
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- Li2HAsO4
- LiHCO3
- Li3H(CO3)2
- LiH2PO3
- LiH2PO4
- LiHSO3
- LiHSO4
- LiHe
- LiI
- LiIO
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- LiIO3
- LiIO4
- Li2IrO3
- Li7La3Zr2O12
- LiMn2O4
- Li2MoO4
- Li0.9Mo6O17
- LiN3
- Li3N
- LiNH2
- Li2NH
- LiNO2
- LiNO3
- LiNO3·H2O
- Li2N2O2
- LiNa
- Li2NaPO3
- LiNaNO2
- LiNbO3
- Li2NbO3
- LiO−
- LiO2
- LiO3
- Li2O
- Li2O2
- LiOH
- Li3P
- LiPF6
- Li3PO4
- Li2HPO3
- Li2HPO4
- Li3PO3
- Li3PO4
- Li2Po
- Li2PtO3
- Li2RuO3
- Li2S
- LiSCN
- LiSH
- LiSO3F
- Li2SO3
- Li2SO4
- Li[SbF6]
- Li2Se
- Li2SeO3
- Li2SeO4
- LiSi
- Li2SiF6
- Li4SiO4
- Li2SiO3
- Li2Si2O5
- LiTaO3
- Li2Te
- LiTe3
- Li2TeO3
- Li2TeO4
- Li2TiO3
- Li4Ti5O12
- LiTi2(PO4)3
- LiVO3·2H2O
- Li3V2(PO4)3
- Li2WO4
- LiYF4
- LiZr2(PO4)3
- Li2ZrO3
- Hemolithin (extraterrestrial protein)
- Organolithium reagents
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- C4H6LiNO4
- LiC2F6NO4S2
- LiN(SiMe3)2
- Li3C6H5O7
- C5H5Li
- LiN(C3H7)2
- (C6H5)2PLi
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- (CH3)3CLi
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- C6H5Li
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- LiO2C(CH2)16CH3
- C4H5LiO4
- LiEt3BH
- LiOC(CH3)3
- C9H18LiN
- LiC2H3 Vinyllithium
- LiC
11H
23COO
- Amblygonite
- Berezanskite
- Brannockite
- Cryolithionite
- Darapiosite
- Darrellhenryite
- Elbaite
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- Fluor-liddicoatite
- Emeleusite
- Eucryptite LiAlSiO4
- Faizievite
- Hectorite
- Hsianghualite
- Jadarite LiNaSiB3O7OH
- Keatite Li(AlSi2O6)
- Kunzite
- Lavinskyite
- Lepidolite
- Lithiophilite LiMnPO4
- Lithiophosphate Li3PO4
- Manandonite
- Manganoneptunite
- Nambulite
- Neptunite
- Olympite
- Petalite LiAlSi4010
- Pezzottaite Cs(Be2Li)Al2Si6O18
- Rossmanite
- Saliotite
- Sogdianite
- Spodumene LiAl(SiO3)2
- Sugilite
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- Tourmaline
- Triphylite LiFePO4
- Zabuyelite Li2CO3
- Zektzerite
- Zinnwaldite
- LixBey
- HLiHe+
- LiFHeO
- LiHe2
- (HeO)(LiF)2
- La2/3-xLi3xTiO3He
- Aluminium–lithium alloys
- Heteroatom-promoted lateral lithiation
- LB buffer
- Lithium atom
- Lithium medication
- LiNixCoyAlzO2
- LiNixMnyCozO2
- Lithium soap
- Lithium Triangle
- Lucifer yellow
- Magnesium–lithium alloys
- NASICON
- Environmentally friendly red light flare