The Grignard reaction is an organometallic chemical reaction in which alkyl, allyl, vinyl, or aryl-magnesium halides add to a carbonyl group in an aldehyde or ketone. This reaction is important for the formation of carbon–carbon bonds. The reaction of an organic halide with magnesium is not a Grignard reaction, but provides a Grignard reagent.
Organolithium reagents are organometallic compounds that contain carbon – lithium bonds. They are important reagents in organic synthesis, and are frequently used to transfer the organic group or the lithium atom to the substrates in synthetic steps, through nucleophilic addition or simple deprotonation. Organolithium reagents are used in industry as an initiator for anionic polymerization, which leads to the production of various elastomers. They have also been applied in asymmetric synthesis in the pharmaceutical industry. Due to the large difference in electronegativity between the carbon atom and the lithium atom, the C-Li bond is highly ionic. Owing to the polar nature of the C-Li bond, organolithium reagents are good nucleophiles and strong bases. For laboratory organic synthesis, many organolithium reagents are commercially available in solution form. These reagents are highly reactive, and are sometimes pyrophoric.
François Auguste Victor Grignard was a Nobel Prize-winning French chemist.
Dimethylformamide is an organic compound with the formula (CH3)2NC(O)H. Commonly abbreviated as DMF (although this initialism is sometimes used for dimethylfuran, or dimethyl fumarate), this colourless liquid is miscible with water and the majority of organic liquids. DMF is a common solvent for chemical reactions. Dimethylformamide is odorless, but technical-grade or degraded samples often have a fishy smell due to impurity of dimethylamine. Dimethylamine degradation impurities can be removed by sparging degraded samples with an inert gas such as argon or by sonicating the samples under reduced pressure. As its name indicates, it is a derivative of formamide, the amide of formic acid. DMF is a polar (hydrophilic) aprotic solvent with a high boiling point. It facilitates reactions that follow polar mechanisms, such as SN2 reactions.
Metalation is a chemical reaction which involves the bonding of a metal atom to what is typically an organic molecule to form a new compound. This reaction usually involves the replacement of a halogen atom in an organic molecule with a metal atom to form an organometallic compound. In the laboratory, metalation is commonly used to activate organic molecules during the formation of C—X bonds, which are necessary for the synthesis of many organic molecules.
The Bamford–Stevens reaction is a chemical reaction whereby treatment of tosylhydrazones with strong base gives alkenes. It is named for the British chemist William Randall Bamford and the Scottish chemist Thomas Stevens Stevens (1900–2000). The usage of aprotic solvents gives predominantly Z-alkenes, while protic solvent gives a mixture of E- and Z-alkenes. As an alkene-generating transformation, the Bamford–Stevens reaction has broad utility in synthetic methodology and complex molecule synthesis.
The Bodroux–Chichibabin aldehyde synthesis is a chemical reaction whereby a Grignard reagent is converted to an aldehyde one carbon longer.
The Bouveault–Blanc reduction is a chemical reaction in which an ester is reduced to primary alcohols using absolute ethanol and sodium metal. It was first reported by Louis Bouveault and Gustave Louis Blanc in 1903. Bouveault and Blanc demonstrated the reduction of ethyl oleate and n-butyl oleate to oleyl alcohol. modified versions of which were subsequently refined and published in Organic Syntheses.
The Blaise ketone synthesis is the chemical reaction of acid chlorides with organozinc compounds to give ketones.
The Ivanov reaction is the chemical reaction of the dianions (endiolates) of aryl acetic acids with electrophiles, primarily carbonyl compounds or isocyanates. The reaction was named after the Bulgarian organic chemist, Academician Dimitar Ivanov, who discovered it.
A Grignard reagent or Grignard compound is a chemical compound with the generic 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−CH
3 and phenylmagnesium bromide (C
6H
5)−Mg−Br. They are a subclass of the organomagnesium compounds
The Finkelstein reaction named after the German chemist Hans Finkelstein, is an SN2 reaction that involves the exchange of one halogen atom for another. It is an equilibrium reaction, but the reaction can be driven to completion by exploiting the differential solubility of halide salts, or by using a large excess of the halide salt.
Organozinc compounds in organic chemistry contain carbon to zinc chemical bonds. Organozinc chemistry is the science of organozinc compounds describing their physical properties, synthesis and reactions.
There are several Akabori amino acid reactions, which are named after Shirō Akabori (1900–1992), a Japanese chemist.
In organic chemistry, the Kumada coupling is a type of cross coupling reaction, useful for generating carbon–carbon bonds by the reaction of a Grignard reagent and an organic halide. The procedure uses transition metal catalysts, typically nickel or palladium, to couple a combination of two alkyl, aryl or vinyl groups. The groups of Robert Corriu and Makoto Kumada reported the reaction independently in 1972.
The Nozaki–Hiyama–Kishi reaction is a nickel/chromium coupling reaction forming an alcohol from the reaction of an aldehyde with an allyl or vinyl halide. In their original 1977 publication, Tamejiro Hiyama and Hitoshi Nozaki reported on a chromium(II) salt solution prepared by reduction of chromic chloride by lithium aluminium hydride to which was added benzaldehyde and allyl chloride:
Electrophilic amination is a chemical process involving the formation of a carbon–nitrogen bond through the reaction of a nucleophilic carbanion with an electrophilic source of nitrogen.
In organic chemistry, carbonyl reduction is the organic reduction of any carbonyl group by a reducing agent.
Louis Bouveault was a French scientist who became professor of organic chemistry at the Faculty of Sciences of the University of Paris. He is known for the Bouveault aldehyde synthesis and the Bouveault–Blanc reduction.
Tamejiro Hiyama is a Japanese organic chemist. He is best known for his work in developing the Nozaki-Hiyama-Kishi reaction and the Hiyama coupling. He is currently a professor at the Chuo University Research and Development Initiative, and a Professor Emeritus of Kyoto University.
