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vinyllithium
Sign in to saveVinyllithium 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.
Chemical data
- Formula
- C2H3Li
- Molecular weight
- 34 g/mol
- SMILES
- [Li].C=[CH]
- InChIKey
- PGOLTJPQCISRTO-UHFFFAOYSA-N
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 34.039
Show 2 more facts
- chemical formula
- C₂H₃Li
- canonical SMILES
- [Li]C=C
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
4 sectionsContents
- Preparation and structure
- Reactions
- Alternative reagents
- 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, especially for vinylations.
==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,
Excerpted from Wikipedia’s “vinyllithium” article, available under the CC BY-SA 4.0 licence.