Vinyllithium
Identifiers | |
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3D model (
JSmol ) |
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3587231 | |
ChEBI | |
ChemSpider | |
ECHA InfoCard
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100.011.844 |
EC Number |
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723 | |
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C2H3Li | |
Molar mass | 33.99 g·mol−1 |
Appearance | white solid |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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pyrophoric |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Vinyllithium is an
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
- ^ ISBN 978-0-471-93623-7..
- .
- .
- .
- doi:10.15227/orgsyn.068.0116.)
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