|
Carbene Dimerization Baratta 1997
In organic chemistry, a carbene is a molecule containing a neutral carbon atom with a valence of two and two unshared valence electrons. The general formula is or where the R represents substituents or hydrogen atoms. The term "carbene" may also refer to the specific compound , also called methylene, the parent hydride from which all other carbene compounds are formally derived. There are two types of carbenes: singlets or triplets, depending upon their electronic structure. The different classes undergo different reactions. Most carbenes are extremely reactive and short-lived. A small number (the dihalocarbenes, carbon monoxide, and carbon monosulfide) can be isolated, and can stabilize as metal ligands, but otherwise cannot be stored in bulk. A rare exception are the persistent carbenes, which have extensive application in modern organometallic chemistry. Generation There are two common methods for carbene generation: α-elimination and small-molecule extrusi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Carbene
In organic chemistry, a carbene is a molecule containing a neutral carbon atom with a Valence (chemistry), valence of two and two unshared valence electrons. The general formula is or where the R represents substituents or hydrogen atoms. The term "carbene" may also refer to the specific compound , also called methylene radical, methylene, the parent hydride from which all other carbene compounds are formally derived. There are two types of carbenes: singlet state, singlets or triplet state, triplets, depending upon their electronic structure. The different classes undergo different reactions. Most carbenes are extremely reactive and short-lived. A small number (the diHalogen, halocarbenes, carbon monoxide, and carbon monosulfide) can be isolated, and can stabilize as Coordination complex, metal ligands, but otherwise cannot be stored in bulk. A rare exception are the persistent carbenes, which have extensive application in modern organometallic chemistry. Generatio ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Simmons–Smith Reaction
The Simmons–Smith reaction is an organic cheletropic reaction involving an organozinc carbenoid that reacts with an alkene (or alkyne) 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. Mechanism Examples Thus, cyclohexene, diiodomethane, and a zinc-copper couple (as iodomethylzinc iodide, ) yield norcarane (bicyclo .1.0eptane). : The Simmons–Smith reaction is generally preferred over other methods of cyclopropanation, however it can be expensive due to the high cost of diiodomethane. Modifications involving cheaper alternatives have been developed, such as dibromomethane or diazomethane and zinc iodide. The reactivity of the system can also be increased by using the Furukawa modification, exchanging ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Zinc
Zinc is a chemical element; it has symbol Zn and atomic number 30. It is a slightly brittle metal at room temperature and has a shiny-greyish appearance when oxidation is removed. It is the first element in group 12 (IIB) of the periodic table. In some respects, zinc is chemically similar to magnesium: both elements exhibit only one normal oxidation state (+2), and the Zn2+ and Mg2+ ions are of similar size. Zinc is the 24th most abundant element in Earth's crust and has five stable isotopes. The most common zinc ore is sphalerite (zinc blende), a zinc sulfide mineral. The largest workable lodes are in Australia, Asia, and the United States. Zinc is refined by froth flotation of the ore, roasting, and final extraction using electricity ( electrowinning). Zinc is an essential trace element for humans, animals, plants and for microorganisms and is necessary for prenatal and postnatal development. It is the second most abundant trace metal in humans after iron, an import ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Lithium Salt
Lithium (from , , ) is a chemical element; it has symbol Li and atomic number 3. It is a soft, silvery-white alkali metal. Under standard conditions, it is the least dense metal and the least dense solid element. Like all alkali metals, lithium is highly reactive and flammable, and must be stored in vacuum, inert atmosphere, or inert liquid such as purified kerosene or mineral oil. It exhibits a metallic luster. It corrodes quickly in air to a dull silvery gray, then black tarnish. It does not occur freely in nature, but occurs mainly as pegmatitic minerals, which were once the main source of lithium. Due to its solubility as an ion, it is present in ocean water and is commonly obtained from brines. Lithium metal is isolated electrolytically from a mixture of lithium chloride and potassium chloride. The nucleus of the lithium atom verges on instability, since the two stable lithium isotopes found in nature have among the lowest binding energies per nucleon of all ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organolithium Reagent
In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important 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. History and ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Geminal
In chemistry, the descriptor geminal () refers to the relationship between two atoms or functional groups that are attached to the same atom. A geminal diol, for example, is a diol (a molecule that has two alcohol functional groups) attached to the same carbon atom, as in methanediol. Also the shortened prefix ''gem'' may be applied to a chemical name to denote this relationship, as in a ''gem''-dibromide for "geminal dibromide". The concept is important in many branches of chemistry, including synthesis and spectroscopy, because functional groups attached to the same atom often behave differently from when they are separated. Geminal diols, for example, are easily converted to ketones or aldehydes with loss of water.Peter Taylor (2002)''Mechanism and synthesis'' Book 10 of ''Molecular world''. Open University, Royal Society of Chemistry; . 368 pages The related term '' vicinal'' refers to the relationship between two functional groups that are attached to adjacent atoms. Thi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Phase-transfer Catalyst
In chemistry, a phase-transfer catalyst or PTC is a catalyst that facilitates the Phase transition, transition of a reactant from one phase (matter), phase into another phase where reaction occurs. Phase-transfer catalysis is a special form of catalysis and can act through homogeneous catalysis or heterogeneous catalysis methods depending on the catalyst used. Ionic compound, Ionic reactants are often soluble in an aqueous phase but insoluble in an organic phase in the absence of the phase-transfer catalyst. The catalyst functions like a detergent for solubilizing the salts into the organic phase. Phase-transfer catalysis refers to the acceleration of the reaction upon the addition of the phase-transfer catalyst. PTC is widely exploited industrially.Marc Halpern "Phase-Transfer Catalysis" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. Polyesters for example are prepared from acyl chlorides and Bisphenol A, bisphenol-A. Phosphothioate-based pesticides a ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Haloform
In chemistry, trihalomethanes (THMs) are chemical compounds in which three of the four hydrogen atoms of methane () are replaced by halogen atoms. Trihalomethanes with all the same halogen atoms are called haloforms. Many trihalomethanes find uses in industry as solvents or refrigerants. Some THMs are also environmental pollutants, and a few are considered carcinogenic. Table of common trihalomethanes Industrial uses Only chloroform has significant applications of the haloforms. In the predominant application, chloroform is required for the production of tetrafluoroethylene (TFE), precursor to teflon. Chloroform is fluorinated by reaction with hydrogen fluoride to produce chlorodifluoromethane (R-22). Pyrolysis of chlorodifluoromethane (at 550-750 °C) yields TFE, with difluorocarbene as an intermediate. :CHCl3 + 2 HF -> CHClF2 + 2 HCl :2 CHClF2 -> C2F4 + 2 HCl Refrigerants and solvents Trihalomethanes released to the environment break down faster than chlorofluorocarbons ( ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydrohalic Acid
In chemistry, hydrogen halides (hydrohalic acids when in the aqueous phase) are diatomic, inorganic compounds that function as Arrhenius acids. The formula is HX where X is one of the halogens: fluorine, chlorine, bromine, iodine, astatine, or tennessine. All known hydrogen halides are gases at standard temperature and pressure.The Acidity of the Hydrogen Halides. (2020, August 21). Retrieved May 5, 2021, from https://chem.libretexts.org/@go/page/3699 Comparison to hydrohalic acids The hydrogen halides are diatomic molecules with no tendency to ionize in the gas phase (although liquified hydrogen fluoride is a polar solvent somewhat similar to water). Thus, chemists distinguish hydrogen chloride from hydrochloric acid. The former is a gas at room temperature that reacts with water to give the acid. Once the acid has formed, the diatomic molecule can be regenerated only with difficulty, but not by normal distillation. Commonly the names of the acid and the molecules are no ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Phenyllithium
Phenyllithium is an organometallic agent with the empirical formula . It is most commonly used as a metalating agent in organic syntheses and a substitute for Grignard reagents for introducing phenyl groups in organic syntheses. Crystalline phenyllithium is colorless; however, solutions of phenyllithium are various shades of brown or red depending on the solvent used and the impurities present in the solute. Preparation Phenyllithium was first produced by the reaction of lithium metal with diphenylmercury: : Reaction of a phenyl halide with lithium metal produces phenyllithium: : Phenyllithium can also be synthesized with a metal-halogen exchange reaction: : The predominant method of producing phenyllithium today are the latter two syntheses. Reactions The primary use of PhLi is to facilitate formation of carbon-carbon bonds by nucleophilic addition and substitution reactions: : 2-Phenylpyridine is prepared by the reaction of phenyl lithium with pyridine, a process that entail ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
