| 词条 | Vinyllithium |
| 释义 |
| ImageFile = Vinyllithium.png | ImageSize = 140 px | ImageAlt = | IUPACName = | OtherNames = |Section1={{Chembox Identifiers | CASNo = 917-57-7 | PubChem = | ChemSpiderID = 10254403 | SMILES = [Li]C=C | StdInChI = 1S/C2H3.Li/c1-2;/h1H,2H2; | StdInChIKey = PGOLTJPQCISRTO-UHFFFAOYSA-N}} |Section2={{Chembox Properties | C=2|H=3|Li=1 | MolarMass = | Appearance = white solid | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = pyrophoric | FlashPt = | AutoignitionPt = }} }}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 structureSolutions 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] ReactionsVinyllithium 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. References1. ^1 {{cite journal|title=Vinyllithium|authors= Eisenhart, Eric K.; Bessieres, Bernard|journal=e-EROS Encyclopedia of Reagents for Organic Synthesis|year=2007|doi=10.1002/047084289X.rv015.pub2}}. 2. ^{{cite journal|title=X-Ray crystal structure of a vinyllithium–tetrahydrofuran solvate (C2H3Li–thf)4. Quantitative estimation of Li–H distances by 6Li–1H HOESY|authors=Walter Bauer, Frank Hampel|journal=J. Chem. Soc., Chem. Commun.|year=1992|pages=903-905|doi=10.1039/C39920000903}} 3. ^{{cite journal|title=Mixed Higher-order Cyanocuprate-induced Epoxide Openings: 1-benzyloxy-4-penten-2-ol|authors=Bruce H. Lipshutz, Robert Moretti, Robert Crow|journal=Org. Synth.|year=1990|volume=69|page=80|doi=10.15227/orgsyn.069.0080}} 2 : Organolithium compounds|Vinyl compounds |
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