Organometallic chemistry is the study of organometallic compounds, chemical compounds containing at least one chemical bond between a carbon atom of an organic molecule and a metal, including alkali, alkaline earth, and transition metals, and sometimes broadened to include metalloids like boron, silicon, and selenium, as well. Aside from bonds to organyl fragments or molecules, bonds to 'inorganic' carbon, like carbon monoxide, cyanide, or carbide, are generally considered to be organometallic as well. Some related compounds such as transition metal hydrides and metal phosphine complexes are often included in discussions of organometallic compounds, though strictly speaking, they are not necessarily organometallic. The related but distinct term "metalorganic compound" refers to metal-containing compounds lacking direct metal-carbon bonds but which contain organic ligands. Metal β-diketonates, alkoxides, dialkylamides, and metal phosphine complexes are representative members of this class. The field of organometallic chemistry combines aspects of traditional inorganic and organic chemistry.
Zinc chloride is an inorganic chemical compound with the formula ZnCl2·nH2O, with n ranging from 0 to 4.5, forming hydrates. Zinc chloride, anhydrous and its hydrates, are colorless or white crystalline solids, and are highly soluble in water. Five hydrates of zinc chloride are known, as well as four forms of anhydrous zinc chloride.
The Simmons–Smith reaction is an organic cheletropic reaction involving an organozinc carbenoid that reacts with an alkene to form a cyclopropane. It is named after Howard Ensign Simmons, Jr. and Ronald D. Smith. It uses a methylene free radical intermediate that is delivered to both carbons of the alkene simultaneously, therefore the configuration of the double bond is preserved in the product and the reaction is stereospecific.
Metalation is a chemical reaction that forms a bond to a metal. This reaction usually refers to the replacement of a halogen atom in an organic molecule with a metal atom, resulting in 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.
Diethyl azodicarboxylate, conventionally abbreviated as DEAD and sometimes as DEADCAT, is an organic compound with the structural formula CH3CH2−O−C(=O)−N=N−C(=O)−O−CH2CH3. Its molecular structure consists of a central azo functional group, RN=NR, flanked by two ethyl ester groups. This orange-red liquid is a valuable reagent but also quite dangerous and explodes upon heating. Therefore, commercial shipment of pure diethyl azodicarboxylate is prohibited in the United States and is carried out either in solution or on polystyrene particles.
The Reformatsky reaction is an organic reaction which condenses aldehydes or ketones with α-halo esters using metallic zinc to form β-hydroxy-esters:
Triethylborane (TEB), also called triethylboron, is an organoborane. It is a colorless pyrophoric liquid. Its chemical formula is (CH3CH2)3B or (C2H5)3B, abbreviated Et3B. It is soluble in organic solvents tetrahydrofuran and hexane.
The Blaise ketone synthesis is the chemical reaction of acid chlorides with organozinc compounds to give ketones.
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.
In organic chemistry, alkyl nitrites are a group of organic compounds based upon the molecular structure R−O−N=O, where R represents an alkyl group. Formally they are alkyl esters of nitrous acid. They are distinct from nitro compounds.
In organic chemistry, cyclopropanation refers to any chemical process which generates cyclopropane rings. It is an important process in modern chemistry as many useful compounds bear this motif; for example pyrethroid insecticides and a number of quinolone antibiotics. However, the high ring strain present in cyclopropanes makes them challenging to produce and generally requires the use of highly reactive species, such as carbenes, ylids and carbanions. Many of the reactions proceed in a cheletropic manner.
The Negishi coupling is a widely employed transition metal catalyzed cross-coupling reaction. The reaction couples organic halides or triflates with organozinc compounds, forming carbon-carbon bonds (C-C) in the process. A palladium (0) species is generally utilized as the catalyst, though nickel is sometimes used. A variety of nickel catalysts in either Ni0 or NiII oxidation state can be employed in Negishi cross couplings such as Ni(PPh3)4, Ni(acac)2, Ni(COD)2 etc.
Organozinc chemistry is the study of the physical properties, synthesis, and reactions of organozinc compounds, which are organometallic compounds that contain carbon (C) to zinc (Zn) chemical bonds.
Organocadmium chemistry describes the physical properties, synthesis, reactions, and use of organocadmium compounds, which are organometallic compounds containing a carbon to cadmium chemical bond. Cadmium shares group 12 with zinc and mercury and their corresponding chemistries have much in common. The synthetic utility of organocadmium compounds is limited.
A Rieke metal is a highly reactive metal powder generated by reduction of a metal salt with an alkali metal. These materials are named after Reuben D. Rieke, who first described along with an associate in 1972 the recipes for their preparation. In 1974 he told about Rieke-magnesium. A 1989 paper by Rieke lists several metals that are allowed by the periodic table to be produced by his process: Cd, Zn, Ni, Pt, Pd, Fe, In, Tl, Co, Cr, Mo, W, Cu, which in turn are called Rieke-nickel, Rieke-platinum, etc.
Diiodomethane or methylene iodide, commonly abbreviated "MI", is an organoiodine compound. Diiodomethane is a very dense colorless liquid; however, it decomposes upon exposure to light liberating iodine, which colours samples brownish. It is slightly soluble in water, but soluble in organic solvents. It has a very high refractive index of 1.741, and a surface tension of 0.0508 N·m−1.
Dimethylzinc, also known as zinc methyl, DMZ, or DMZn, is a toxic organozinc compound with the chemical formula Zn(CH3)2. It belongs to the large series of similar compounds such as diethylzinc.
Zinc–copper couple is an alloy of zinc and copper that is employed as a reagent in organic synthesis. The “couple” was popularized after the report by Simmons and Smith, published in 1959, on its application as an activated source of zinc required for formation of an organozinc reagent in the Simmons–Smith cyclopropanation of alkenes. The couple has been widely applied as a reagent in other reactions requiring activated zinc metal. Zinc–copper couple does not refer to a rigorously defined chemical structure or alloy composition. The couple may contain varying proportions of copper and zinc; the zinc content is typically greater than 90%, although an alloy containing similar proportions of zinc and copper is used in some cases. The couple is frequently prepared as a darkly-colored powder and is slurried in an ethereal solvent prior to being used in slight excess relative to the substrate. Activation of zinc by copper is essential to the couple’s utility, but the origin of this effect is poorly documented. It is speculated that copper enhances reactivity of zinc at the surface of the alloy.
Zinc compounds are chemical compounds containing the element zinc which is a member of the group 12 of the periodic table. The oxidation state of zinc in most compounds is the group oxidation state of +2. Zinc may be classified as a post-transition main group element with zinc(II). Zinc compounds are noteworthy for their nondescript appearance and behavior: they are generally colorless, do not readily engage in redox reactions, and generally adopt symmetrical structures.
Main group organometallic chemistry concerns the preparation and properties of main-group elements directly bonded to carbon. The inventory is large. The compounds exhibit a wide range of properties, including ones that are water-stable and others that are pyrophoric. Many are very useful themselves, as chemical reagents, or as catalysts.
