Organometallic compounds used in organic synthesis
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 organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride Cl−Mg−CH3 and phenylmagnesium bromide (C6H5)−Mg−Br. They are a subclass of the organomagnesium compounds.
Grignard compounds are popular reagents in organic synthesis for creating new carbon–carbon bonds. For example, when reacted with another halogenated compound R'−X' in the presence of a suitable catalyst, they typically yield R−R' and the magnesium halide MgXX' as a byproduct; and the latter is insoluble in the solvents normally used. In this aspect, they are similar to organolithium reagents.
Grignard reagents are rarely isolated as solids. Instead, they are normally handled as solutions in solvents such as diethyl ether or tetrahydrofuran using air-free techniques. Grignard reagents are complex with the magnesium atom bonded to two ether ligands as well as the halide and organyl ligands.
The discovery of the Grignard reaction in 1900 was recognized with the Nobel Prize awarded to Victor Grignard in 1912.
Grignardreagents or Grignard compounds are chemical compounds with the general formula R−Mg−X, where X is a halogen and R is an organic group, normally...
definition, carbon alkyl, allyl, vinyl, or aryl magnesium halides (Grignardreagent) are added to the carbonyl groups of either an aldehyde or ketone under...
Victor Grignard (6 May 1871 – 13 December 1935) was a French chemist who won the Nobel Prize for his discovery of the eponymously named Grignardreagent and...
highly flammable, colorless, and moisture sensitive material is the Grignardreagent derived from isopropyl chloride. It is commercially available, usually...
reaction, useful for generating carbon–carbon bonds by the reaction of a Grignardreagent and an organic halide. The procedure uses transition metal catalysts...
substance. Examples include the Collins reagent, Fenton's reagent, and Grignardreagents. In analytical chemistry, a reagent is a compound or mixture used to...
magnesium selenide are similar. The name of the Grignardreagent comes from the French chemist Victor Grignard who discovered it. This type of organomagnesium...
usually with acid- or base-catalysis. Carbonation of a Grignardreagent and organolithium reagents: RLi + CO2 → RCO−2Li+ RCO−2Li+ + HCl → RCO2H + LiCl Halogenation...
> "Experiment 9: Synthesis of Benzoic Acid via Carbonylation of a GrignardReagent" (PDF). University of Wisconsin-Madison. Archived from the original...
They are commonly found as Grignardreagents, formed by reaction of magnesium with haloalkanes. Examples of Grignardreagents are phenylmagnesium bromide...
with magnesium metal in dry ether to form allylmagnesium bromide, a Grignardreagent: CH2=CHCH2Br + Mg → CH2=CHCH2MgBr Allyl bromide reacts with benzene...
diethyl ether or tetrahydrofuran (THF). Phenylmagnesium bromide is a Grignardreagent. It is often used as a synthetic equivalent for the phenyl "Ph−" synthon...
the conjugate addition of Grignardreagents in 1941, organocopper reagents have emerged as weakly basic, nucleophilic reagents for substitution and addition...
This is a list of inorganic and organic reagents commonly used in chemistry. Reagents are "substances or compounds that are added to a system in order...
solids.[citation needed] These reagents are useful because, unlike related Grignardreagents and organolithium reagents, they react with organic halides...
reaction of ortho-substituted nitroarenes and nitrosoarenes with vinyl Grignardreagents to form substituted indoles. The reaction is often unsuccessful without...
Ethylmagnesium bromide is a Grignardreagent with formula C2H5MgBr. It is widely used in the laboratory synthesis of organic compounds. Apart from acting...
Georg Wittig, and Henry Gilman. In comparison with Grignard (magnesium) reagents, organolithium reagents can often perform the same reactions with increased...
developed by Victor Grignard, involving the use of a GrignardreagentGrignardreagent, an organomagnesium compound developed by Victor Grignard. All pages with...
Arens–van Dorp synthesis the compound ethoxyacetylene is converted to a Grignardreagent and reacted with a ketone, the reaction product is a propargyl alcohol...
flammable, colorless, and moisture sensitive material is the simplest Grignardreagent and is commercially available, usually as a solution in tetrahydrofuran...
treatment of this species with an organometallic reagent such as a Grignardreagent or organolithium reagent. Nahm and Weinreb also reported the synthesis...
from trifluoroborane (in ether) and the ethyl or pentafluorophenyl Grignardreagent. Further carbanion addition will effect a borate (R4B−). Boronic acids...
chlorine group is then reacted with magnesium turnings to form a Grignardreagent. This Grignard is carboxylated and the resulting product is worked up to synthesize...
reaction of esters with dialkyldialkoxytitanium reagents, which are generated in situ from Grignardreagents containing a hydrogen in beta-position and titanium(IV)...
situ, whereas a Grignard reagent is prepared separately before addition of the carbonyl compound. Unlike many Grignardreagents, the organometallic species...
Global Information