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A solution of a carbonyl compound is added to a Grignard reagent. (See gallery) An example of a Grignard reaction (R 2 or R 3 could be hydrogen). The Grignard reaction (French:) is an organometallic chemical reaction in which, according to the classical definition, carbon alkyl, allyl, vinyl, or aryl magnesium halides (Grignard reagent) are added to the carbonyl groups of either an aldehyde or ...
Usually Grignard reagents are written as R-Mg-X, but in fact the magnesium(II) centre is tetrahedral when dissolved in Lewis basic solvents, as shown here for the bis-adduct of methylmagnesium chloride and THF. Grignard reagents or Grignard compounds are chemical compounds with the general formula R−Mg−X, where X is a halogen and R is an ...
Trimethylsilyl chloride, also known as chlorotrimethylsilane is an organosilicon compound (silyl halide), with the formula (CH 3) 3 SiCl, often abbreviated Me 3 SiCl or TMSCl. It is a colourless volatile liquid that is stable in the absence of water. It is widely used in organic chemistry.
Trimethylsilylacetylene is commercially available. It may also be prepared in a manner similar to other silyl compounds: deprotonation of acetylene with a Grignard reagent, followed by reaction with trimethylsilyl chloride. [4] Trimethylsilylacetylene is a precursor to 1,4-bis(trimethylsilyl)buta-1,3-diyne, a protected form of 1,3-butadiyne. [5]
Structure of the organoscandium complex with two (trimethylsilyl)methyl ligands, (C 5 H 5)Sc(CH 2 TMS) 2 (THF). [8] Color scheme: O (red), Sc (blue), Si (orange). (Trimethylsilyl)methyllithium is widely used in organotransition metal chemistry to affix (trimethylsilyl)methyl ligands.
The products after silylation, namely silyl ethers and silyl amines, are resilient toward basic conditions. [2] Protection is typically done by reacting the functional group with a silyl halide by an SN2 reaction mechanism, typically in the presence of base. [3] The protection mechanism begins with the base deprotonating the alcohol group.
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Organolithium reagents are also better than Grignard reagents in their ability to react with carboxylic acids to form ketones. [36] This reaction can be optimized by carefully controlling the amount of organolithium reagent addition, or using trimethylsilyl chloride to quench excess lithium reagent. [40]