Loading AI tools
Chemical compound From Wikipedia, the free encyclopedia
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]
![]() | |
Identifiers | |
---|---|
3D model (JSmol) |
|
3587231 | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.011.844 |
EC Number |
|
723 | |
PubChem CID |
|
CompTox Dashboard (EPA) |
|
| |
| |
Properties | |
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).
|
Solutions of vinyllithium are prepared by lithium-halogen exchange reactions. A halide-free route entails reaction of tetravinyltin with butyllithium:
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]
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]
Vinyl magnesium bromide, a Grignard reagent, is in many ways easier to generate in the laboratory and behaves similarly to vinyllithium.[5]
Seamless Wikipedia browsing. On steroids.
Every time you click a link to Wikipedia, Wiktionary or Wikiquote in your browser's search results, it will show the modern Wikiwand interface.
Wikiwand extension is a five stars, simple, with minimum permission required to keep your browsing private, safe and transparent.