Organoalkali metal compounds

The nature of the catalyst and certain experimental observations, such as product distribution [Eq. (5.61)], indicate a carbanionic reaction mechanism. A benzylic carbanion formed through proton abstraction by an organoalkali metal compound... 

Organoalkali metal compounds may also be obtained from reactions between organomercury compounds and the elemental metals. 

Preparation of dialkylmagnesium compounds from organoalkali metal compounds... 

Organoalkali metal compound Magnesium component" Product Ref. 

General Aspects of the Chemistry of Organoalkali Metal Compounds... 

The formation of the metal hahde as a by-product limits the use of this method for the synthesis of reagents intended for further reactions. The relative solubihties of the organoalkali metal compounds and the metal hahdes formed in these reactions do not generally allow for easy separations. 

The direct reaction of an organic molecule with an alkali metal produces an organoalkali metal compound and hydrogen gas (equation 5). 

The reaction of an organo- or amido-alkah metal reagent with an acidic organic molecule produces an organoalkali metal compound and the amine or organic compound (equation 7). 

Methyl lithium and butyl lithium are widely used for the synthesis of other organolithium compounds. For example, lithium cyclopentadienides are generally prepared by the reaction of the cyclopentadiene with butyl lithium. In contrast, the amido-alkali metal compounds are becoming increasingly important in the synthesis of organoalkali metal compounds with the heavier alkali metals. For example, l,2,4-tris(trimethylsilyl)-l,3-cyclopentadiene reacts with potassium bis(trimethylsilyl)amide to form potassium l,2,4-tris(trimethylsilyl)cyclopentadienide. ... 

By reacting directly with the alkali metal, organomercury compounds are commonly used to synthesize organoalkali metal compounds of the heavier alkali metals. This route has been used to make various alkyl compounds, such as butyl and trimethylsilylmethyl derivatives (equation 10). 

Organoalkali metal compounds of the heavier alkah metals with more highly substituted alkyl groups can be formed from the reaction of an alkane with the appropriate methyl derivative (MMe M = Na, K, Rb, and Cs ) (equation 18). 

Organoalkali metal compound Magnesium component0 Product Ref. 

Metalation of Weak Acids. The ability to metalate very weak acids is a property which has been used widely for the direct synthesis of organolithium compounds, for new or improved organic syntheses, for polymer grafting, and for telomerizations involving chain transfer by transmetalation. These major topics are covered in seven chapters of this volume, indicating both the scope and utility of this property of N-chelated organoalkali metal compounds. 

GENERAL ASPECTS OF THE CHEMISTRY OF ORGANOALKALI METAL COMPOUNDS... 

The direct reaction of an organic halide with an alkali metal is one of the most important methods for synthesizing organolithium compounds. The reaction of two equivalents of the alkali metal with one equivalent of the organohalide produces the organoalkali metal compound and metal halide... 

There are three general types of metallation reactions (metal-hydrogen exchange) that are commonly used to synthesize organoalkali metal compounds from organic molecules Direct reaction with an alkali metal, reaction with an alkali metal hydride, or reaction with an organo- or amido-alkali metal. Since these reactions involve acid/base equilibria, they are dependent on both the C-H acidity of the organic molecule and the basicity of the alkali metal source. 

The structures of organolithium compounds have been extensively studied, and there are a number of reviews avaUable. A recent review of the structures of organoalkali metal compounds of the heavier group 1 metals has also been made available. Specific details of the structures formed by various types of organoalkali metal compounds both in... 

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