Trimethylsilylmethyl potassium

Elimination of the proton from 1, 4-diene or 1, 3-diene compounds is often used for the preparation of metal dienyl complexes. The following compounds are utilized as deprotonating reagents alkyllithium compounds, (trimethylsilylmethyl )potassium, alkali metal amides, etc. Also useful are alkali metals as sands in the presence of triethylamine, which prevents anionic polymerization of dienes. 

Dichlorodimethyltitanium, 216 Intramolecular alkylation 9-Bromo-9-phenylfluorene, 48 Chloromethyl ethyl ether, 75 Di-p-carbonylhexacarbonyldicobalt, 99 l-Hydroxy-3-trimethylsilylmethyl-3-butene, 147 Menthol, 172 Potassium t-butoxide, 252 Miscellaneous alkylations at active hydrogens... 

Trunethylsilylmethylpotassium, KCH2Si(CH3)3. This base is prepared by reduction of bis(trimethylsilylmethyl)mercury with potassium sand. It is comparable in reactivity to n-BuLi/KOC(CH,)3 for allylic and benzylic metallation. ... 

Destlylation. Anhydrous cesium fluoride desilylates trimethylsilylmethyl-sulfonium, trimethylsilylmethylammonium, and trimethylsilylmethylphosphonium salts at room temperature to produce ylides, which undergo various useful transformations. Use of potassium fluoride-18-crown-6 or a tetraalkylammonium fluoride gives products in low yield in these reactions. The trimethylsilylmethyl-onium salts are prepared by alkylation of sulfides, amines, imines, and phosphines with (trifluoromethanesulfonylmethyl)trimethylsilane (1). 

ISOPREPENYLATION Aluminum chloride. Aluminum chloride-Potassium pheno-xide. Carbon disulfide-Methyl iodide. 2-Trimethylsilylmethyl-l, 3-butadiene. 2-Trimethylsilylmethylenecyclobutane. 

This organopotassium reagent is obtained as a grey suspension by reaction of bis(trimethylsilylmethyl)mercury (Fluka) with potassium/sodium alloy (5 1 by weight) in pentane for 30 min. A similar reaction with sodium metal is slower. ... 

Anionic organogallium(i) species have been obtained by reductive elimination from tris(trimethylsilylmethyl)gallium and alkali-metal hydrides in benzene or DME [equation 10)]. Molecular-weight measurements show that the potassium... 

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