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1,1-Bis(chloromethyl)ethylene
1,1-Bis(chloromethyl)ethylene is the organic compound with the formula CH2=C(CH2Cl)2. It is a colorless liquid. Featuring two allylic chloride substituents, it is dialkylating agent. Synthesis and reactions It is prepared from pentaerythritol via a multistep procedure, beginning with the partial chlorination. The compound reacts with diiron nonacarbonyl to give the complex of trimethylenemethane Fe(η4-C(CH2)3)(CO)3. It is also a precursor to .1.1propellane In organic chemistry, propellane is any member of a class of polycyclic hydrocarbons, whose carbon skeleton consists of three rings of carbon atoms sharing a common carbon–carbon covalent bond. The concept was introduced in 1966 by D. Ginsbu .... References {{DEFAULTSORT:Bis(chloromethyl)ethylene, 1,1- Chloroalkenes Allyl compounds ...
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Trimethylenemethane
Trimethylenemethane (often abbreviated TMM) is a chemical compound with formula . It is a neutral free molecule with two unsatisfied valence bonds, and is therefore a highly reactive free radical. Formally, it can be viewed as an isobutylene molecule with two hydrogen atoms removed from the terminal methyl groups. Structure The electronic structure of trimethylenemethane was discussed in 1948.C. A. Coulson (1948), Journal de Chimie Physique et de Physico-Chimie Biologique, volume 45, page 243. Cited by Slipchenko and Krylov (2003) It is a neutral four-carbon molecule containing four pi molecular orbitals. When trapped in a solid matrix at about , the six hydrogen atoms of the molecule are equivalent. Thus, it can be described either as zwitterion, or as the simplest conjugated hydrocarbon that cannot be given a Kekulé structure. It can be described as the superposition of three states: It has a triplet ground state (3''A''2′/3''B''2), and is therefore a diradic ...
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Organic Compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon- hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds comprise the discipline known as organic chemistry. For historical reasons, a few classes of carbon-containing compounds (e.g., carbonate salts and cyanide salts), along with a few other exceptions (e.g., carbon dioxide, hydrogen cyanide), are not classified as organic compounds and are considered inorganic. Other than those just named, little consensus exists among chemists on precisely which carbon-containing compounds are excluded, making any rigorous definition of an organic compound elusive. Although organic compounds make up only a small percentage of Earth's crust, they are of central importance because all known life is based on organic compounds. Livin ...
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Alkylating Agent
Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting alkylation. Alkyl groups can also be removed in a process known as dealkylation. Alkylating agents are often classified according to their nucleophilic or electrophilic character. In oil refining contexts, alkylation refers to a particular alkylation of isobutane with olefins. For upgrading of petroleum, alkylation produces a premium blending stock for gasoline. In medicine, alkylation of DNA is used in chemotherapy to damage the DNA of cancer cells. Alkylation is accomplished with the class of drugs called alkylating antineoplastic agents. Nucleophilic alkylating agents Nucleophilic alkylating agents deliver the equivalent of an alkyl anion (carbanion). The formal "alkyl anion" attacks an electrophile, forming a new covalent bon ...
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Pentaerythritol
Pentaerythritol is an organic compound with the formula C(CH2OH)4. Classified as a polyol, it is a white solid. Pentaerythritol is a building block for the synthesis and production of explosives, plastics, paints, appliances, cosmetics, and many other commercial products. The word pentaerythritol is a blend of ''penta-'' in reference to its 5 carbon atoms and ''erythritol'', which also possesses 4 alcohol groups. Synthesis Pentaerythritol was first reported in 1891 by German chemist Bernhard Tollens and his student P. Wigand. It may be prepared via a base-catalyzed multiple- addition reaction between acetaldehyde and 3 equivalents of formaldehyde to give pentaerythrose (CAS: 3818-32-4), followed by a Cannizzaro reaction with a fourth equivalent of formaldehyde to give the final product. Uses Pentaerythritol is a versatile building block for the preparation of many compounds, particularly polyfunctionalized derivatives. applications include alkyd resins, varnishes, polyv ...
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Diiron Nonacarbonyl
Diiron nonacarbonyl is an organometallic compound with the formula Fe2(CO)9. This metal carbonyl is an important reagent in organometallic chemistry and of occasional use in organic synthesis. It is a more reactive source of Fe(0) than Fe(CO)5. This micaceous orange solid is virtually insoluble in all common solvents. Synthesis and structure Following the original method, photolysis of an acetic acid solution of Fe(CO)5 produces Fe2(CO)9 in good yield:King, R. B. Organometallic Syntheses. Volume 1 Transition-Metal Compounds; Academic Press: New York, 1965. . :2 Fe(CO)5 → Fe2(CO)9 + CO Fe2(CO)9 consists of a pair of Fe(CO)3 centers linked by three bridging CO ligands. Although older textbooks show an Fe-Fe bond consistent with the 18 electron rule (8 valence electrons from Fe, two each from the terminal carbonyls, one each from the bridging carbonyls and one from the other Fe atom in the metal-metal bond), theoretical analyses have consistently indicated the absence of ...
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Propellane
In organic chemistry, propellane is any member of a class of polycyclic hydrocarbons, whose carbon skeleton consists of three rings of carbon atoms sharing a common carbon–carbon covalent bond. The concept was introduced in 1966 by D. Ginsburg Propellanes with small cycles are highly strained and unstable, and are easily turned into polymers with interesting structures, such as staffanes. Partly for these reasons, they have been the object of much research. Nomenclature The name derives from a supposed resemblance of the molecule to a propeller: namely, the rings would be the propeller's blades, and the shared C–C bond would be its axis. The bond shared by the three cycles is usually called the "bridge"; the shared carbon atoms are then the "bridgeheads". The IUPAC nomenclature of the homologue series of all-carbon propellanes would be called tricyclo .y.z.01,(x+2)lkane. More common in literature is the notation means the member of the family whose rings have ''x'', ...
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