Ring-closing Metathesis
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Ring-closing Metathesis
Ring-closing metathesis (RCM) is a widely used variation of olefin metathesis in organic chemistry for the synthesis of various unsaturated rings via the intramolecular metathesis of two terminal alkenes, which forms the cycloalkene as the ''E-'' or ''Z-'' isomers and volatile ethylene.Carey, F. A.; Sunburg, R. J. Reactions Involving Transition Metals. ''Advanced Organic Chemistry: Reaction and Synthesis'', 5th Ed.; Part B; Springer: New York, 2010, pp. 761-767.Monfette, S.; Fogg, D. E. (2009). "Equilibrium Ring-Closing Metathesis". ''Chem. Rev.'' 109 (8): 3783-3816. . The most commonly synthesized ring sizes are between 5-7 atoms;Deiters, A.; Martin, S. F. (2004). “Synthesis of Oxygen- and Nitrogen-Containing Heterocycles by Ring-Closing Metathesis”. ''Chem. Rev.'' 104 (5): 2199-2238. . however, reported syntheses include 45- up to 90- membered macroheterocycles.Cain, M. F.; Forrest, W. P.; Peryshkov, R. V.; Schrock, R. R. Muller, P. (2013). “Synthesis of a TREN in Whic ...
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Olefin Metathesis
Olefin metathesis is an organic reaction that entails the redistribution of fragments of alkenes (olefins) by the scission and regeneration of carbon-carbon double bonds. Because of the relative simplicity of olefin metathesis, it often creates fewer undesired by-products and hazardous wastes than alternative organic reactions. For their elucidation of the reaction mechanism and their discovery of a variety of highly active catalysts, Yves Chauvin, Robert H. Grubbs, and Richard R. Schrock were collectively awarded the 2005 Nobel Prize in Chemistry. Catalysts The reaction requires metal catalysts. Most commercially important processes employ heterogeneous catalysts. The heterogeneous catalysts are often prepared by in-situ activation of a metal halides (MClx) using organoaluminium or organotin compounds, e.g. combining MClx–EtAlCl2. A typical catalyst support is alumina. Commercial catalysts are often based on molybdenum and ruthenium. Well-defined organometallic co ...
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Olefin Metathesis
Olefin metathesis is an organic reaction that entails the redistribution of fragments of alkenes (olefins) by the scission and regeneration of carbon-carbon double bonds. Because of the relative simplicity of olefin metathesis, it often creates fewer undesired by-products and hazardous wastes than alternative organic reactions. For their elucidation of the reaction mechanism and their discovery of a variety of highly active catalysts, Yves Chauvin, Robert H. Grubbs, and Richard R. Schrock were collectively awarded the 2005 Nobel Prize in Chemistry. Catalysts The reaction requires metal catalysts. Most commercially important processes employ heterogeneous catalysts. The heterogeneous catalysts are often prepared by in-situ activation of a metal halides (MClx) using organoaluminium or organotin compounds, e.g. combining MClx–EtAlCl2. A typical catalyst support is alumina. Commercial catalysts are often based on molybdenum and ruthenium. Well-defined organometallic co ...
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Organic Synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one of the most important branches of organic chemistry. There are several main areas of research within the general area of organic synthesis: ''total synthesis'', ''semisynthesis'', and ''methodology''. Total synthesis A total synthesis is the complete chemical synthesis of complex organic molecules from simple, commercially available petrochemical or natural precursors. Total synthesis may be accomplished either via a linear or convergent approach. In a ''linear'' synthesis—often adequate for simple structures—several steps are performed one after another until the molecule is complete; the chemical compounds made in each step are called synthetic intermediates. Most often, each step in a synthesis refers to a separate rea ...
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Grubbs' Catalyst
Grubbs catalysts are a series of transition metal carbene complexes used as catalysts for olefin metathesis. They are named after Robert H. Grubbs, the chemist who supervised their synthesis. Several generations of the catalyst have been developed. Grubbs catalysts tolerate many functional groups in the alkene substrates, are air-tolerant, and are compatible with a wide range of solvents. For these reasons, Grubbs catalysts have become popular in synthetic organic chemistry. Grubbs, together with Richard R. Schrock and Yves Chauvin, won the Nobel Prize in Chemistry in recognition of their contributions to the development of olefin metathesis. First-generation catalyst In the 1960s, ruthenium trichloride was found to catalyze olefin metathesis. Processes were commercialized based on these discoveries. These ill-defined but highly active homogeneous catalysts remain in industrial use. The first well-defined ruthenium catalyst was reported in 1992. It was prepared from RuCl2(PPh ...
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Grubbs Initial RCM Syntheses
Grubbs may refer to: People * Grubbs (surname) In fiction * Grubbs Grady, a main character in ''The Demonata'' series of novels * Verla Grubbs, a character in the ''All My Children'' TV series Other uses * Grubbs catalyst, a series of transition metal carbene complexes used as catalysts for olefin metathesis * Grubbs's test for outliers, a statistical test used to detect outliers * Grubb's Tramway (Mowbray), a tramway in northern Tasmania * Grubb's Tramway (Zeehan), a tramway in western Tasmania * Grubbs, Arkansas Grubbs is a city in Jackson County, Arkansas, United States. The population was 386 at the 2010 census. Geography According to the United States Census Bureau, the town has a total area of 1.4 km2 (0.6 mi2), all land. Demographics As ... * Grubbs Corner, West Virginia * '' United States v. Grubbs'', a 2006 United States Supreme Court case See also * Grubb (other) {{disambiguation ...
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Le Chatelier's Principle
Le Chatelier's principle (pronounced or ), also called Chatelier's principle (or the Equilibrium Law), is a principle of chemistry used to predict the effect of a change in conditions on chemical equilibria. The principle is named after French chemist Henry Louis Le Chatelier, and sometimes also credited to Karl Ferdinand Braun, who discovered it independently. It can be stated as: Phenomena in apparent contradiction to Le Chatelier's principle can also arise in systems of simultaneous equilibrium (see response reactions). Le Chatelier's principle is sometimes alluded to in discussions of topics other than thermodynamics. Thermodynamic statement The Le Chatelier–Braun principle analyzes the qualitative behaviour of a thermodynamic system when a designated one of its externally controlled state variables, say L, changes by an amount \Delta L, the 'driving change', causing a change \delta_ M, the 'response of prime interest', in its conjugate state variable M, all other exte ...
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Entropy
Entropy is a scientific concept, as well as a measurable physical property, that is most commonly associated with a state of disorder, randomness, or uncertainty. The term and the concept are used in diverse fields, from classical thermodynamics, where it was first recognized, to the microscopic description of nature in statistical physics, and to the principles of information theory. It has found far-ranging applications in chemistry and physics, in biological systems and their relation to life, in cosmology, economics, sociology, weather science, climate change, and information systems including the transmission of information in telecommunication. The thermodynamic concept was referred to by Scottish scientist and engineer William Rankine in 1850 with the names ''thermodynamic function'' and ''heat-potential''. In 1865, German physicist Rudolf Clausius, one of the leading founders of the field of thermodynamics, defined it as the quotient of an infinitesimal amount of hea ...
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Amides
In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. It can be viewed as a derivative of a carboxylic acid () with the hydroxyl group () replaced by an amine group (); or, equivalently, an acyl (alkanoyl) group () joined to an amine group. Common examples of amides are acetamide (), benzamide (), and dimethylformamide (). Amides are qualified as primary, secondary, and tertiary according to whether the amine subgroup has the form , , or , where R and R' are groups other than hydrogen. The core of amides is called the amide group (specifically, carboxamide group). Amides are pervasive in nature and technology. Proteins and important plastics ...
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Pyrroline
Pyrrolines, also known under the name dihydropyrroles, are three different heterocyclic organic chemical compounds that differ in the position of the double bond. Pyrrolines are formally derived from the aromate pyrrole by hydrogenation. 1-Pyrroline is a cyclic imine, whereas 2-pyrroline and 3-pyrroline are cyclic amines. Substituted pyrrolines Notable examples of pyrrolines containing various substituents include: * 2-Acetyl-1-pyrroline, an aroma compound with a white bread-like smell * Thienamycin, a beta-lactam antibiotic * MTSL, a chemical used for certain NMR experiments * Pyrrolysine, an unusual proteinogenic amino acid * 1-Pyrroline-5-carboxylic acid, a biosynthetic metabolite * Porphyrin, consisting of two alternating pairs of pyrrol and pyrroline connected via methine (=CH-) bridges ''N''-substituted pyrrolines can be generated by ring-closing metathesis.Marcelle L. Ferguson, Daniel J. O'leary, And Robert H. Grubbs "Ring-closing Metathesis Synthesis Of N-boc-3-pyrroli ...
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Dihydropyran
In organic chemistry, dihydropyran refers to two heterocyclic compounds with the chemical formula, formula C5H8O: *3,4-Dihydropyran, 3,4-Dihydro-2''H''-pyran *3,6-dihydro-2''H''-pyran Nomenclature In IUPAC names, "dihydro" refers to the two added hydrogen atoms needed to remove one double bond from the parent compound pyran. The numbers in front of the prefix indicate the position of the added hydrogen atoms (and not the position of the double bonds). The italicized capital ''H'' denotes the "indicated hydrogen", which is a second hydrogen atom present on the location where no double bond is present.A Guide to IUPAC Nomenclature of Organic Compounds (Recommendations 1993)''R-1.3 Indicated Hydrogen''/ref> See also *Pyran *Tetrahydropyran References

{{DEFAULTSORT:Dihydropyran, 2, 3- Dihydropyrans, ...
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Gregory Fu
Gregory (Greg) C. Fu is a Professor of organic chemistry at the California Institute of Technology and the Norman Chandler Professor of Chemistry. The current research interests of the Fu laboratory include metal-catalyzed coupling reactions and the design of chiral catalysts. In particular, the group is focused on the development of nickel-catalyzed enantioselective cross-couplings of alkyl electrophiles and on photoinduced, copper-catalyzed carbon–heteroatom bond-forming reactions. The group works in collaboration with the laboratory of Professor Jonas C. Peters. In 2014, he was elected as a member of the National Academy of Sciences.. He was awarded an Arthur C. Cope Scholar Award in 1998-1999. He was awarded the Elias J. Corey Award from the American Chemical Society in 2004. Education Gregory Fu received his BS from the Massachusetts Institute of Technology in 1985, where he worked in the laboratory of Professor Karl Barry Sharpless, then completed his PhD at Harvard U ...
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