Vinyllithium

Summary

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]

Vinyllithium
Vinyllithium.png
Identifiers
  • 917-57-7
3D model (JSmol)
  • Interactive image
3587231
ChEBI
  • CHEBI:51472
ChemSpider
  • 10254403
EC Number
  • 213-028-5
723
  • 637931
  • InChI=1S/C2H3.Li/c1-2;/h1H,2H2;
    Key: PGOLTJPQCISRTO-UHFFFAOYSA-N
  • [Li]C=C
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).
Infobox references

Preparation and structureEdit

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.

ReactionsEdit

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]

ReferencesEdit

  1. ^ a b Eisenhart, Eric K.; Bessieres, Bernard (2007). "Vinyllithium". E-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rv015.pub2. ISBN 978-0471936237.{{cite journal}}: 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. (12): 903–905. doi:10.1039/C39920000903.{{cite journal}}: 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.