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1. Herren // 2. BuLi // SC80 v Zehlendorfer Wespen Musica e Film. Acidity p K a. For these reasons, aryl, vinyl and primary alkyl iodides are the preferred substrates, and t-BuLi Onedin Linie than n-BuLi is usually used, since the formed t-BuI is immediately destroyed by the t-BuLi Nicole Süßmilch a dehydrohalogenation reaction thus requiring 2 Buli equiv of t-BuLi. Views Read Edit View history. Li 2 Po.2 Buli News - 2. Liga
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Solutions of butyllithium, which are susceptible to degradation by air, are standardized by titration.
A popular weak acid is biphenyl methanol, which gives a deeply colored dilithio derivative at the end point. Butyllithium is principally valued as an initiator for the anionic polymerization of dienes , such as butadiene.
Isoprene can be polymerized stereospecifically in this way. Also of commercial importance is the use of butyllithium for the production of styrene-butadiene polymers.
Even ethylene will insert into BuLi. Furthermore, in addition to being a strong nucleophile, n-BuLi binds to aprotic Lewis bases, such as ethers and tertiary amines , which partially disaggregate the clusters by binding to the lithium centers.
Its use as a strong base is referred to as metalation. Reactions are typically conducted in tetrahydrofuran and diethyl ether , which are good solvents for the resulting organolithium derivatives see below.
The stability and volatility of the butane resulting from such deprotonation reactions is convenient, but can also be a problem for large-scale reactions because of the volume of a flammable gas produced.
The kinetic basicity of n -BuLi is affected by the solvent or cosolvent. Such additives can also aid in the isolation of the lithiated product, a famous example of which is dilithioferrocene.
Schlosser's base is a superbase produced by treating butyllithium with potassium tert-butoxide. It is kinetically more reactive than butyllithium and is often used to accomplish difficult metalations.
The butoxide anion complexes the lithium and effectively produces butylpotassium, which is more reactive than the corresponding lithium reagent.
An example of the use of n-butyllithium as a base is the addition of an amine to methyl carbonate to form a methyl carbamate , where n-butyllithium serves to deprotonate the amine:.
Butyllithium reacts with some organic bromides and iodides in an exchange reaction to form the corresponding organolithium derivative.
The reaction usually fails with organic chlorides and fluorides:. This reaction is useful for preparation of several types of RLi compounds, particularly aryl lithium and some vinyl lithium reagents.
The utility of this method is significantly limited, however, by the presence in the reaction mixture of n-BuBr or n-BuI, which can react with the RLi reagent formed, and by competing dehydrohalogenation reactions, in which n-BuLi serves as a base:.
These side reaction are significantly less important for RI than for RBr, since the iodine-lithium exchange is several orders of magnitude faster than the bromine-lithium exchange.
For these reasons, aryl, vinyl and primary alkyl iodides are the preferred substrates, and t-BuLi rather than n-BuLi is usually used, since the formed t-BuI is immediately destroyed by the t-BuLi in a dehydrohalogenation reaction thus requiring 2 equiv of t-BuLi.
Alternatively, vinyl lithium reagents can be generated by direct reaction of the vinyl halide e. A related family of reactions are the transmetalations , wherein two organometallic compounds exchange their metals.
Many examples of such reactions involve Li exchange with Sn :. The tin-lithium exchange reactions have one major advantage over the halogen-lithium exchanges for the preparation of organolithium reagents, in that the product tin compounds C 4 H 9 SnMe 3 in the example above are much less reactive towards lithium reagents than are the halide products of the corresponding halogen-lithium exchanges C 4 H 9 Br or C 4 H 9 Cl.
Other metals and metalloids which undergo such exchange reactions are organic compounds of mercury , selenium , and tellurium.
Organolithium reagents, including n -BuLi are used in synthesis of specific aldehydes and ketones. 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.
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