Vinyllithium (original) (raw)
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Vinyllithium
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|---|---|
| Identifiers | |
| CAS Number | 917-57-7 |
| 3D model (JSmol) | Interactive image |
| Beilstein Reference | 3587231 |
| ChEBI | CHEBI:51472 |
| ChemSpider | 10254403 |
| ECHA InfoCard | 100.011.844  |
| EC Number | 213-028-5 |
| Gmelin Reference | 723 |
| PubChem CID | 637931 |
| CompTox Dashboard (EPA) | DTXSID10238670 |
| InChI InChI=1S/C2H3.Li/c1-2;/h1H,2H2;Key: PGOLTJPQCISRTO-UHFFFAOYSA-N | |
| SMILES [Li]C=C | |
| 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 |
Chemical compound
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
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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]
Structure of [LiC2H3(THF)]4.
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
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Vinyl magnesium bromide, a Grignard reagent, is in many ways easier to generate in the laboratory and behaves similarly to vinyllithium.[5]
- ^ 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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