Diethylsuccinoylsuccinate
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Diethylsuccinoylsuccinate
Diethylsuccinoylsuccinate is an organic compound with the formula H2C(OH)=C(CO2Et)sub>2 (Et = ethyl). A tetrasubstituted derivative of 1,4-cyclohexadiene, the compound is the enol tautomer of the corresponding cyclohexadione. It is produced by base-induced condensation of diethyl succinate: :2 EtO2CCH2CH2CO2Et H2C(OH)=C(CO2Et)sub>2 + 2 EtOH Diethylsuccinylsuccinate is valued as a precursor to the quinacridone pigments. For example, it reacts with two equiv of aniline Aniline is an organic compound with the formula C6 H5 NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine In organic chemistry, an aromatic amine is an organic compound consisting of an aroma ...s to give the diamines H2C(N(H)Ar)=C(CO2Et)sub>2, which undergoes cyclization upon treatment with acid to give dihydroquinacridone. When heated in the presence of acid, diethylsuccinoylsuccinate converts to 1,4-cyclohexanedione via hydrolysis of the esters fo ...
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Quinacridone
Quinacridone is an organic compound used as a pigment. Numerous derivatives constitute the quinacridone pigment family, which finds extensive use in industrial colorant applications such as robust outdoor paints, inkjet printer ink, tattoo inks, artists' watercolor paints, and color laser printer toner. As pigments, the quinacridones are insoluble. The development of this family of pigments supplanted the alizarin dyes. Synthesis The name indicates that the compounds are a fusion of acridone and quinoline, although they are not made that way. Classically the parent is prepared from the 2,5-dianilide of terephthalic acid (C6H2(NHPh)2(CO2H)2). Condensation of succinosuccinate esters with aniline followed by cyclization affords dihydroquinacridone, which are readily dehydrogenated. The latter is oxidized to quinacridone. Derivatives of quinacridone can be readily obtained by employing substituted anilines. Linear ''cis''-Quinacridones can be prepared from isophtha ...
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Diethyl Succinate
Diethyl succinate is the diethyl ester of succinate. It is a colorless liquid with the formula (CH2CO2Et)2 (Et = ethyl Ethyl may refer to: Arts and entertainment * Cold Ethyl, a Swedish rock band *Ethyl Sinclair, a character in the ''Dinosaurs'' television show Science and technology * Ethyl group, an organic chemistry moiety * Ethyl alcohol (or ethanol) * E ...). The organic molecule contains two ester groups. This ester is a versatile chemical intermediate. A colorless liquid, diethyl succinate is formed by Fisher esterification of succinic acid and ethanol. Reactions Being a diester, diethyl succinate is a particularly versatile building block. It participates in acyloin condensation to give 2-hydroxycyclobutanone. Via condensation with oxalate esters, it serves as a precursor to ketoglutaric acid. 222px, left, Diethylsuccinoylsuccinate, a useful precursor to dyes and pigments, is produced by base-induced condensation of diethyl succinate. References {{ref ...
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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. Living t ...
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Ethyl Group
In organic chemistry, an ethyl group (abbr. Et) is an alkyl substituent with the formula , derived from ethane (). ''Ethyl'' is used in the International Union of Pure and Applied Chemistry's nomenclature of organic chemistry for a saturated two-carbon moiety in a molecule, while the prefix "''eth-''" is used to indicate the presence of two carbon atoms in the molecule. Ethylation Ethylation is the formation of a compound by introduction of the ethyl group. The most widely practiced example of this reaction is the ethylation of benzene with ethylene to yield ethylbenzene, a precursor to styrene, which is a precursor to polystyrene. Approximately 24.7 million tons of ethylbenzene were produced in 1999. :: Many ethyl-containing compounds are generated by electrophilic ethylation, i.e. treatment of nucleophiles with sources of Et+. Triethyloxonium tetrafluoroborate t3OF4 is such a reagent. For good nucleophiles, less electrophilic reagents are employed, such as ethyl h ...
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1,4-cyclohexadiene
1,4-Cyclohexadiene is an organic compound with the formula C6H8. It is a colourless, flammable liquid that is of academic interest as a prototype of a large class of related compounds called terpenoids, an example being γ-terpinene. An isomer of this compound is 1,3-cyclohexadiene. Synthesis and reactions In the laboratory, substituted 1,4-cyclohexadienes are synthesized by Birch reduction of related aromatic compounds using an alkali metal dissolved in liquid ammonia and a proton donor such as an alcohol. In this way, over reduction to the fully saturated ring is avoided. 1,4-Cyclohexadiene and its derivatives are easily aromatized, the driving force being the formation of an aromatic ring. The conversion to an aromatic system may be used to trigger other reactions, such as the Bergman cyclization The Masamune-Bergman cyclization or Masamune-Bergman reaction or Masamune-Bergman cycloaromatization is an organic reaction and more specifically a rearrangement reaction taking p ...
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Enol
In organic chemistry, alkenols (shortened to enols) are a type of reactive structure or intermediate in organic chemistry that is represented as an alkene ( olefin) with a hydroxyl group attached to one end of the alkene double bond (). The terms ''enol'' and ''alkenol'' are portmanteaus deriving from "-ene"/"alkene" and the "-ol" suffix indicating the hydroxyl group of alcohols, dropping the terminal "-e" of the first term. Generation of enols often involves removal of a hydrogen adjacent (α-) to the carbonyl group—i.e., deprotonation, its removal as a proton, . When this proton is not returned at the end of the stepwise process, the result is an anion termed an enolate (see images at right). The enolate structures shown are schematic; a more modern representation considers the molecular orbitals that are formed and occupied by electrons in the enolate. Similarly, generation of the enol often is accompanied by "trapping" or masking of the hydroxy group as an ether, such as ...
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Tautomer
Tautomers () are structural isomers (constitutional isomers) of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the relocation of a hydrogen atom within the compound. The phenomenon of tautomerization is called tautomerism, also called desmotropism. Tautomerism is for example relevant to the behavior of amino acids and nucleic acids, two of the fundamental building blocks of life. Care should be taken not to confuse tautomers with depictions of "contributing structures" in chemical resonance. Tautomers are distinct chemical species that can be distinguished by their differing atomic connectivities, molecular geometries, and physicochemical and spectroscopic properties, whereas resonance forms are merely alternative Lewis structure (valence bond theory) depictions of a single chemical species, whose true structure is best described as the "average" of the idealized, hypothe ...
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Aniline
Aniline is an organic compound with the formula C6 H5 NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine In organic chemistry, an aromatic amine is an organic compound consisting of an aromatic ring attached to an amine. It is a broad class of compounds that encompasses aniline Aniline is an organic compound with the formula C6 H5 NH2. Consi .... It is an industrially significant Commodity chemicals, commodity chemical, as well as a versatile starting material for fine chemical synthesis. Its main use is in the manufacture of precursors to polyurethane, dyes, and other industrial chemicals. Like most volatile amines, it has the odor of rotten fish. It Combustion, ignites readily, burning with a smoky flame characteristic of aromatic compounds. It is toxic to humans. Relative to benzene, it is electron-rich. It thus participates more rapidly in electrophilic aromatic substitution reactions. Likewise, it is also prone ...
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