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).
|
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]
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]
{{
cite journal}}
: CS1 maint: multiple names: authors list (
link)
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).
|
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]
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]
{{
cite journal}}
: CS1 maint: multiple names: authors list (
link)