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Template:DISPLAYTITLE:sec-Butyllithium sec-Butyllithium is the chemical compound with the formula CH3CHLiCH2CH3, abbreviated sec-BuLi or s-BuLi This organolithium reagent is used as a source of sec-butyl carbanion in organic synthesis.
Additional recommended knowledge
The carbon-lithium bond is highly polar, rendering the carbon very nucleophilic and basic, as in other organolithium reagents. Sec-butyllithium is more basic than primary organolithium reagents such as n-butyl lithium. It is also more sterically hindered, though it is still useful for syntheses.
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 its solutions of n-BuLi are stable. Many transformatins involving sec-butyllithium are similar to those involving other organolithium reagents. For example, sec-BuLi react with carbonyl compounds and esters to form alcohols. With copper(I) iodide sec-BuLi forms lithium di-sec-butylcuprates. The first two reactions can also be accomplished by using sec-butylmagnesium bromide, a Grignard reagent; in fact, the latter is the typical reagent for this purpose.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Sec-Butyllithium". A list of authors is available in Wikipedia.|