Vinyllithium

Vinyllithium
Identifiers
CAS Number	917-57-7;
3D model (JSmol)	Interactive image;
ChemSpider	10254403;
ECHA InfoCard	100.011.844
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

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.^[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, being a precursor to vinylsilanes, vinylcuprates, and vinylstannanes.^[3] It adds to ketones compounds to give allylic alcohols.

References

^ ^a ^b "Vinyllithium". e-EROS Encyclopedia of Reagents for Organic Synthesis. 2007. doi:10.1002/047084289X.rv015.pub2. {{cite journal}}: Cite uses deprecated parameter |authors= (help).
^ "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.: 903–905. 1992. doi:10.1039/C39920000903. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
^ "Mixed Higher-order Cyanocuprate-induced Epoxide Openings: 1-benzyloxy-4-penten-2-ol". Org. Synth. 69: 80. 1990. doi:10.15227/orgsyn.069.0080. {{cite journal}}: Cite uses deprecated parameter |authors= (help)

[eEROS-1] "Vinyllithium". e-EROS Encyclopedia of Reagents for Organic Synthesis. 2007. doi:10.1002/047084289X.rv015.pub2. {{cite journal}}: Cite uses deprecated parameter |authors= (help).

[2] "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.: 903–905. 1992. doi:10.1039/C39920000903. {{cite journal}}: Cite uses deprecated parameter |authors= (help)

[3] "Mixed Higher-order Cyanocuprate-induced Epoxide Openings: 1-benzyloxy-4-penten-2-ol". Org. Synth. 69: 80. 1990. doi:10.15227/orgsyn.069.0080. {{cite journal}}: Cite uses deprecated parameter |authors= (help)

[1]

[2]

[3]