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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 ...
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.
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]
TMSCl is reactive toward nucleophiles, resulting in the replacement of the chloride. In a characteristic reaction of TMSCl, the nucleophile is water, resulting in hydrolysis to give the hexamethyldisiloxane: + + The related reaction of trimethylsilyl chloride with alcohols can be exploited to produce anhydrous solutions of hydrochloric acid in alcohols, which find use in the mild synthesis of ...
The reaction is named for Pierre Bruylants (1855–1950), [2] who first reported it in 1924. [3] The reaction mechanism appears to involve ejection of the nitrile to form an iminium that is then attacked by the Grignard rather than a direct displacement such as an S N 2 reaction.
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.
Reacting a silyl enol ether with PhSCl, a good and soft electrophile, provides a carbonyl compound sulfenylated at an alpha carbon. [22] [20] In this reaction, the trimethylsilyl group of the silyl enol ether is removed by the chloride ion released from the PhSCl upon attack of its electrophilic sulfur atom. [20]