Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
Methyllithium is the simplest organolithium reagent, with the empirical formula CH3Li. This s-block organometallic compound adopts an oligomeric structure both in solution and in the solid state. This highly reactive compound, invariably used in solution with an ether as the solvent, is a reagent in organic synthesis as well as organometallic chemistry. Operations involving methyllithium require anhydrous conditions, because the compound is highly reactive towards water. Oxygen and carbon dioxide are also incompatible with MeLi. Methyllithium is usually not prepared, but purchased as a solution in various ethers.
Methyllithium is the simplest organolithium reagent, with the empirical formula CH3Li. This s-block organometallic compound adopts an oligomeric structure...
the reaction of an aziridine carrying a methylene bromide group with methyllithium: In this reaction one equivalent of acetylene is lost. Ferrier rearrangement...
structures. For example, methyllithium, ethyllithium and tert-butyllithium all exist in the tetramer [RLi]4. Methyllithium exists as tetramers in a cubane-type...
consisted of treating cyclopentadiene with methyllithium in dimethyl ether and then with dichloromethane and methyllithium in diethyl ether at −45 °C. It can...
basic. The pKa of C5H5PH+ and C5H5NH+ are respectively −16.1 and +5.2. Methyllithium adds to phosphorus in phosphorine whereas it adds to the 2-position...
prepared by treating cadmium dihalides with methyl Grignard reagents or methyllithium. CdBr2 + 2 CH3MgBr → Cd(CH3)2 + 2 MgBr2 The same method was used in...
silyl enol ethers, can also be generated from silyl enol ethers using methyllithium. The reaction occurs via nucleophilic substitution at the silicon of...
NaI It can also be obtained by alkylation of mercuric chloride with methyllithium: HgCl2 + 2 LiCH3 → Hg(CH3)2 + 2 LiCl The molecule adopts a linear structure...
commercially available. An example of an organolithium compound is methyllithium ((CH3Li)x), which exists in tetrameric (x = 4, tetrahedral) and hexameric...
dimethylcopper (CH3)2CuLi can be prepared by adding copper(I) iodide to methyllithium in tetrahydrofuran at −78 °C. In the reaction depicted below, the Gilman...
reduced with sodium borohydride to create racemic hydroxy acid. Excess methyllithium is then added to create methyl ketones which when reduced with lithium...
deprotonated in solution, but the conjugate base is known in forms such as methyllithium. A variety of positive ions derived from methane have been observed...
nucleophilic methyl reagents. Strongly nucleophilic methylating agents include methyllithium (CH3Li) or Grignard reagents such as methylmagnesium bromide (CH3MgX)...
of MeMgI has been somewhat superseded by the commercially available methyllithium. MeI can also be used to prepare dimethylmercury, by reacting 2 moles...
oxygen atoms to give a tetrahedrally bonded magnesium center. Like methyllithium, it is the synthetic equivalent to the methyl carbanion synthon. It...
common e.g. lithium fluoride, lithium hydroxide, lithium amide, and methyllithium, but lithium boryllides are extraordinarily rare. Strong bases do not...
prepared by the salt metathesis reaction of methylmagnesium chloride or methyllithium with titanocene dichloride: Cp2TiCl2 + 2 CH3MgCl → Cp2Ti(CH3)2 + 2 MgCl2...
product with retention of configuration: Of recent date are chiral methyllithium compounds: The phosphate 1 contains a chiral group with a hydrogen and...
Tanzanian royalty Meli Bogileka, Fijian politician Meli email client Methyllithium, organolithium compound Amomyrtus meli, a species of tree Meli Park...
acetonitrile to the sulfuranyl dication 2 followed by reaction with methyllithium in tetrahydrofuran to (a stable) persulfurane 3 as the cis isomer. X-ray...
bond lengths are unusually short with 152 picometers. Reaction with methyllithium with tetrakis(trimethylsilyl)tetrahedrane yields tetrahedranyllithium...
followed by two successive reactions with chlorocarbene generated from methyllithium and dichloromethane to spiro compound 5. Spiropentadiene was trapped...
complex of a boron compound is called a borate. Thus trimethylborane and methyllithium react to form the ate compound Li+B(CH3)−4, lithium tetramethylborate(1-)...
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