Vinyllithium

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

Structure of [LiC₂H₃(THF)]₄.

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. Vinylmagnesium bromide is often used in place of vinyllithium.[4]

gollark: I think my existing version is shorter.

gollark: Oh, no, pointfree.io did it for me.

gollark: ```haskell\text -> concat $ inits text ++ tails text```

gollark: ...

gollark: Fiiiine...

References

Eisenhart, Eric K.; Bessieres, Bernard (2007). "Vinyllithium". e-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rv015.pub2.CS1 maint: uses authors parameter (link).
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.: 903–905. doi:10.1039/C39920000903.CS1 maint: uses authors parameter (link)
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.

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[eEROS-1] Eisenhart, Eric K.; Bessieres, Bernard (2007). "Vinyllithium". e-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rv015.pub2.CS1 maint: uses authors parameter (link).

[2] 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.: 903–905. doi:10.1039/C39920000903.CS1 maint: uses authors parameter (link)

[3] 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.

[4] Dietmar Seyferth (1959). "Di-n-butyldivinyltin". Org. Synth. 39: 10. doi:10.15227/orgsyn.039.0010.