[{"@context":"http:\/\/schema.org\/","@type":"BlogPosting","@id":"https:\/\/wiki.edu.vn\/en\/wiki24\/2015\/08\/23\/sec-butyllithium-wikipedia\/#BlogPosting","mainEntityOfPage":"https:\/\/wiki.edu.vn\/en\/wiki24\/2015\/08\/23\/sec-butyllithium-wikipedia\/","headline":"sec-Butyllithium &#8211; Wikipedia","name":"sec-Butyllithium &#8211; Wikipedia","description":"From Wikipedia, the free encyclopedia Chemical compound sec-Butyllithium is an organometallic compound with the formula CH3CHLiCH2CH3, abbreviated sec-BuLi or s-BuLi.","datePublished":"2015-08-23","dateModified":"2015-08-23","author":{"@type":"Person","@id":"https:\/\/wiki.edu.vn\/en\/wiki24\/author\/lordneo\/#Person","name":"lordneo","url":"https:\/\/wiki.edu.vn\/en\/wiki24\/author\/lordneo\/","image":{"@type":"ImageObject","@id":"https:\/\/secure.gravatar.com\/avatar\/c9645c498c9701c88b89b8537773dd7c?s=96&d=mm&r=g","url":"https:\/\/secure.gravatar.com\/avatar\/c9645c498c9701c88b89b8537773dd7c?s=96&d=mm&r=g","height":96,"width":96}},"publisher":{"@type":"Organization","name":"Enzyklop\u00e4die","logo":{"@type":"ImageObject","@id":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","url":"https:\/\/wiki.edu.vn\/wiki4\/wp-content\/uploads\/2023\/08\/download.jpg","width":600,"height":60}},"image":{"@type":"ImageObject","@id":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/a\/ab\/Sec_Butyllithium_synthesis_01.svg\/400px-Sec_Butyllithium_synthesis_01.svg.png","url":"https:\/\/upload.wikimedia.org\/wikipedia\/commons\/thumb\/a\/ab\/Sec_Butyllithium_synthesis_01.svg\/400px-Sec_Butyllithium_synthesis_01.svg.png","height":"68","width":"400"},"url":"https:\/\/wiki.edu.vn\/en\/wiki24\/2015\/08\/23\/sec-butyllithium-wikipedia\/","wordCount":2869,"articleBody":"From Wikipedia, the free encyclopediaChemical compoundsec-Butyllithium is an organometallic compound with the formula CH3CHLiCH2CH3, abbreviated sec-BuLi or s-BuLi. This chiral organolithium reagent is used as a source of sec-butyl carbanion in organic synthesis.[1]Table of ContentsSynthesis[edit]Properties[edit]Physical properties[edit]Chemical properties[edit]Applications[edit]References[edit]Synthesis[edit]sec-BuLi can be prepared by the reaction of sec-butyl halides with lithium metal:[2]Properties[edit]Physical properties[edit]sec-Butyllithium is a colorless viscous liquid.[1][3] Using mass spectrometry, it was determined that the pure compound has a tetrameric structure.[4] It also exists as tetramers when dissolved in organic solvents such as benzene, cyclohexane or cyclopentane.[3] The cyclopentane solution has been detected with 6Li-NMR spectroscopy to have a hexameric structure at temperatures below \u221241 \u00b0C.[5] In electron-donating solvents such as tetrahydrofuran, there exists an equilibrium between monomeric and dimeric forms.[6]Chemical properties[edit]The carbon-lithium bond is highly polar, rendering the carbon basic, as in other organolithium reagents.  Sec-butyllithium is more basic than the primary organolithium reagent, n-butyllithium.  It is also more sterically hindered. sec-BuLi is employed for deprotonations of particularly weak carbon acids where the more conventional reagent n-BuLi is unsatisfactory.  It is, however, so basic that its use requires greater care than for  n-BuLi.  For example diethyl ether is attacked by sec-BuLi at room temperature in minutes, whereas ether solutions of  n-BuLi are stable.[1]The compound decomposes slowly at room temperature and more rapidly at higher temperatures, giving lithium hydride and a mixture of butenes.[7][8]Applications[edit]Many transformations involving sec-butyllithium are similar to those involving other organolithium reagents.In combination with sparteine as a chiral auxiliary, sec-butyllithium is useful in enantioselective deprototonations.[9]  It is also effective for lithiation of arenes.[10]References[edit]^ a b c Ovaska, T. V. (2001). &#8220;s-Butyllithium&#8221;. Encyclopedia of Reagents for Organic Synthesis. New York: John Wiley &#038; Sons. doi:10.1002\/047084289X.rb397. ISBN\u00a00471936235..^ Hay, D. R.; Song, Z.; Smith, S. G.; Beak, P. (1988). &#8220;Complex-induced proximity effects and dipole-stabilized carbanions: kinetic evidence for the role of complexes in the \u03b1-lithiations of carboxamides&#8221;. J. Am. Chem. Soc. 110 (24): 8145\u20138153. doi:10.1021\/ja00232a029.^ a b Wietelmann, Ulrich; Bauer, Richard J. (2000-06-15), &#8220;Lithium and Lithium Compounds&#8221;,  in Wiley-VCH Verlag GmbH &#038; Co. KGaA (ed.), Ullmann&#8217;s Encyclopedia of Industrial Chemistry, Weinheim, Germany: Wiley-VCH Verlag GmbH &#038; Co. KGaA, pp.\u00a0a15_393, doi:10.1002\/14356007.a15_393, ISBN\u00a0978-3-527-30673-2, retrieved 2022-05-07^ Plavsic, D.; Srzic, D.; Klasinc, Leo (1986). &#8220;Mass spectrometric investigations of alkyllithium compounds in the gas phase&#8221;. The Journal of Physical Chemistry. 90 (10): 2075\u20132080. doi:10.1021\/j100401a020. ISSN\u00a00022-3654.^ Fraenkel, Gideon; Henrichs, Mark; Hewitt, Michael; Su, Biing Ming (1984). &#8220;Structure and dynamic behavior of a chiral alkyllithium compound: carbon-13 and lithium-6 NMR of sec-butyllithium&#8221;. Journal of the American Chemical Society. 106 (1): 255\u2013256. doi:10.1021\/ja00313a052. ISSN\u00a00002-7863.^ Bauer, Walter.; Winchester, William R.; Schleyer, Paul von R. (1987-11-01). &#8220;Monomeric organolithium compounds in tetrahydrofuran: tert-butyllithium, sec-butyllithium, supermesityllithium, mesityllithium, and phenyllithium. Carbon-lithium coupling constants and the nature of carbon-lithium bonding&#8221;. Organometallics. 6 (11): 2371\u20132379. doi:10.1021\/om00154a017. ISSN\u00a00276-7333.^ Glaze, William H.; Lin, Jacob; Felton, E. G. (1965). &#8220;The Thermal Decomposition of sec-Butyllithium&#8221;. The Journal of Organic Chemistry. 30 (4): 1258\u20131259. doi:10.1021\/jo01015a514. ISSN\u00a00022-3263.^ Glaze, William H.; Lin, Jacob; Felton, E. G. (1966). &#8220;The Pyrolysis of Unsolvated Alkyllithium Compounds&#8221;. The Journal of Organic Chemistry. 31 (8): 2643\u20132645. doi:10.1021\/jo01346a044. ISSN\u00a00022-3263.^ Cr\u00e9py, Karen V. L.; Imamoto, Tsuneo (2005). &#8220;Preparation of (S,S)-1,2-bis(tert-Butylmethylphosphino)ethane ((S,S)-t-bu-bisp*) as a Rhodium Complex&#8221;. Organic Syntheses. 82: 22. doi:10.15227\/orgsyn.082.0022.^ Wang, X.; de Silva, S. O.; Reed, J. N.; Billadeau, R.; Griffen, E. J.; Chan, A.; Snieckus, V. (1995). &#8220;7-Methoxyphthalide&#8221;. Org. Synth. 72: 163. doi:10.15227\/orgsyn.072.0163."},{"@context":"http:\/\/schema.org\/","@type":"BreadcrumbList","itemListElement":[{"@type":"ListItem","position":1,"item":{"@id":"https:\/\/wiki.edu.vn\/en\/wiki24\/#breadcrumbitem","name":"Enzyklop\u00e4die"}},{"@type":"ListItem","position":2,"item":{"@id":"https:\/\/wiki.edu.vn\/en\/wiki24\/2015\/08\/23\/sec-butyllithium-wikipedia\/#breadcrumbitem","name":"sec-Butyllithium &#8211; Wikipedia"}}]}]