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Carbometalation
Carbometalation
Carbometalation
(less often carbometallation) is an organometallic reaction involving the nucleophilic addition to alkenes and alkynes of a diverse range of organometallic reagents such as organolithium compounds, organocopper compounds and Grignard reagents according to the following general alkyne scheme:The addition can yield the cis or trans isomer and with unsymmetrical alkynes the organometallic compound can add in two different way thus control of regioselectivity is important. In a follow-up step the sensitive metalalkenyl group is replaced by an electrophile E+. Scope[edit] In one study methylphenylacetylene is reacted with phenylmagnesium bromide to a vinyl magnesium bromide which is quenched with water:[1][2]Another demonstration of this reaction type is an alternative route to tamoxifen starting from diphenylacetylene and ethyllithium:[3]The capturing electrophile here is triisopropyl borate forming the boronic acid R–B(OH)2
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Organic Chemistry
Organic chemistry
Organic chemistry
is a chemistry subdiscipline involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.[1] Study of structure includes many physical and chemical methods to determine the chemical composition and the chemical constitution of organic compounds and materials. Study of properties includes both physical properties and chemical properties, and uses similar methods as well as methods to evaluate chemical reactivity, with the aim to understand the behavior of the organic matter in its pure form (when possible), but also in solutions, mixtures, and fabricated forms
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Borate
Borates are the name for a large number of boron-containing oxyanions. The term "borates" may also refer to tetrahedral boron anions, or more loosely to chemical compounds which contain borate anions of either description. Larger borates are composed of trigonal planar BO3 or tetrahedral BO4 structural units, joined together via shared oxygen atoms[1] and may be cyclic or linear in structure. Boron
Boron
most often occurs in nature as borates, such as borate minerals and borosilicates.Contents1 Structures 2 Boric acid 3 Polymeric ions 4 Borosilicates 5 Minerals and uses 6 Borate
Borate
esters 7 See also 8 References 9 External linksStructures[edit]Idealized structure of a compound with trigonal planar molecular geometry.The simplest borate anion, the orthoborate(3-) ion, [BO3]3-, is known in the solid state, for example in Ca3(BO3)2.[2] In this it adopts a near trigonal planar structure
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Migratory Insertion
A migratory insertion is a type of reaction in organometallic chemistry wherein two ligands on a metal complex combine. It is a subset of reactions that very closely resembles the insertion reactions, and both are differentiated by the mechanism that leads to the resulting stereochemistry of the products
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Nucleophilic Addition
In organic chemistry, a nucleophilic addition reaction is an addition reaction where a chemical compound with an electron-deficient or electrophilic double or triple bond, a π bond, reacts with electron-rich reactant, termed a nucleophile, with disappearance of the double bond and creation of two new single, or σ, bonds
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Chemistry
Chemistry
Chemistry
is the scientific discipline involved with compounds composed of atoms, i.e. elements, and molecules, i.e. combinations of atoms: their composition, structure, properties, behavior and the changes they undergo during a reaction with other compounds.[1][2] Chemistry
Chemistry
addresses topics such as how atoms and molecules interact via chemical bonds to form new chemical compounds. There are four types of chemical bonds: covalent bonds, in which compounds share one or more electron(s); ionic bonds, in which a compound donates one or more electrons to another compound to produce ions: cations and anions; hydrogen bonds; and Van der Waals force
Van der Waals force
bonds
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Copper(I) Chloride
Copper(I) chloride, commonly called cuprous chloride, is the lower chloride of copper, with the formula CuCl. The substance is a white solid sparingly soluble in water, but very soluble in concentrated hydrochloric acid. Impure samples appear green due to the presence of copper(II) chloride.[7]Contents1 History 2 Synthesis 3 Properties 4 Uses4.1 In organic synthesis 4.2 In polymer chemistry5 References 6 External linksHistory[edit] Copper(I) chloride
Copper(I) chloride
was first prepared by Robert Boyle
Robert Boyle
in the mid-seventeenth century[8] from mercury(II) chloride ("Venetian sublimate") and copper metal:HgCl2 + 2 Cu → 2 CuCl + HgIn 1799, J.L. Proust characterized the two different chlorides of copper
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Organoiron Chemistry
Organoiron chemistry
Organoiron chemistry
is the chemistry of iron compounds containing a carbon-to-iron chemical bond.[1][2] Organoiron compounds are relevant in organic synthesis as reagents such as iron pentacarbonyl, diiron nonacarbonyl and disodium tetracarbonylferrate. Iron
Iron
adopts oxidation states from Fe(−II) through to Fe(VII)
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Organophosphine
Organophosphorus compounds are organic compounds containing phosphorus.[1] They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. These compounds are highly effective insecticides, though some are also lethal to humans at minuscule doses (nerve gas) and include some of the most toxic substances ever created by man, including sarin and VX nerve agents.[2] Organophosphorus chemistry is the corresponding science of the properties and reactivity of organophosphorus compounds. Phosphorus, like nitrogen, is in group 15 of the periodic table, and thus phosphorus compounds and nitrogen compounds have many similar properties.[3][4][5] The definition of organophosphorus compounds is variable, which can lead to confusion
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Acetylacetonate
Acetylacetone
Acetylacetone
is an organic compound that exists in two tautomeric forms that interconvert rapidly and are treated as a single compound in most applications. Although the compound is formally named as the diketone form, pentane-2,4-dione, the enol form forms a substantial component of the material[2] and is actually the favored form in many solvents. It is a colourless liquid that is a precursor to acetylacetonate (acac), a common bidentate ligand. It is also a building block for the synthesis of heterocyclic compounds.Contents1 Properties1.1 Tautomerism 1.2 Acid–base properties2 Preparation 3 Reactions3.1 Condensations 3.2 Coordination chemistry4 Biodegradation 5 References 6 External linksProperties[edit] Tautomerism[edit]The keto and enol forms of acetylacetone coexist in solution; these forms are tautomers
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Digital Object Identifier
In computing, a Digital Object Identifier or DOI is a persistent identifier or handle used to uniquely identify objects, standardized by the International Organization for Standardization
International Organization for Standardization
(ISO).[1] An implementation of the Handle System,[2][3] DOIs are in wide use mainly to identify academic, professional, and government information, such as journal articles, research reports and data sets, and official publications though they also have been used to identify other types of information resources, such as commercial videos. A DOI aims to be "resolvable", usually to some form of access to the information object to which the DOI refers. This is achieved by binding the DOI to metadata about the object, such as a URL, indicating where the object can be found. Thus, by being actionable and interoperable, a DOI differs from identifiers such as ISBNs and ISRCs which aim only to uniquely identify their referents
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J. Am. Chem. Soc.
The Journal of the American Chemical Society
American Chemical Society
(also known as JACS) is a weekly peer-reviewed scientific journal that was established in 1879 by the American Chemical Society.[1] The journal has absorbed two other publications in its history, the Journal of Analytical and Applied Chemistry
Chemistry
(July 1893) and the American Chemical Journal (January 1914). It publishes original research papers in all fields of chemistry. Since 2002, the journal is edited by Peter J. Stang (University of Utah).[2] In 2014, the journal moved to a hybrid open access publishing model. Abstracting and indexing[edit] The Journal of the American Chemical Society
American Chemical Society
is abstracted and indexed in Chemical Abstracts Service, Scopus, EBSCOhost, Thomson-Gale, ProQuest, PubMed, Web of Science, and SwetsWise
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Suzuki Reaction
The Suzuki reaction
Suzuki reaction
is an organic reaction, classified as a coupling reaction, where the coupling partners are a boronic acid and an organohalide catalyzed by a palladium(0) complex.[1][2][3] It was first published in 1979 by Akira Suzuki and he shared the 2010 Nobel Prize in Chemistry with Richard F. Heck
Richard F. Heck
and Ei-ichi Negishi
Ei-ichi Negishi
for their effort for discovery and development of palladium-catalyzed cross couplings in organic synthesis.[4] In many publications this reaction also goes by the name Suzuki–Miyaura reaction and is also referred to as the Suzuki coupling. It is widely used to synthesize poly-olefins, styrenes, and substituted biphenyls
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Boronic Acid
A boronic acid is a compound related to boric acid in which one of the three hydroxyl groups is replaced by an alkyl or aryl group.[1] As a compound containing a carbon–boron bond, members of this class thus belong to the larger class of organoboranes. Boronic acids act as Lewis acids. Their unique feature is that they are capable of forming reversible covalent complexes with sugars, amino acids, hydroxamic acids, etc. (molecules with vicinal, (1,2) or occasionally (1,3) substituted Lewis base donors (alcohol, amine, carboxylate)). The pKa of a boronic acid is ~9, but they can form tetrahedral boronate complexes with pKa ~7. They are occasionally used in the area of molecular recognition to bind to saccharides for fluorescent detection or selective transport of saccharides across membranes. Boronic acids are used extensively in organic chemistry as chemical building blocks and intermediates predominantly in the Suzuki coupling
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J. Org. Chem.
The Journal of Organic Chemistry, colloquially known as JOC or J Org, is a peer-reviewed[1] scientific journal for original contributions of fundamental research in all branches of theory and practice[2] in organic and bioorganic chemistry. It is published by the publishing arm of the American Chemical Society, with 24 issues per year. According to the Journal Citation
Citation
Reports, the journal had a 2016 impact factor of 4.849[3] and it is the journal that received the most cites (99,193 in 2016) in the field of organic chemistry.[2] According to Web of Knowledge
Web of Knowledge
(and as December 2012), eleven papers from the journal have received more than 1,000 citations, with the most cited paper[4] having received 7,967 citations. The current Editor-in-Chief is Scott J. Miller from Yale University.[5] Indexing[edit] J. Org. Chem
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Organolithium
Organolithium reagents are organometallic compounds that contain carbon – lithium bonds. They are important reagents 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.[1] 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.[2] Due to the large difference in electronegativity between the carbon atom and the lithium atom, the C-Li bond is highly ionic. This extremely polar nature of the C-Li bond makes organolithium reagents good nucleophiles and strong bases. For laboratory organic synthesis, many organolithium reagents are commercially available in solution form
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