Directing Group
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Directing Group
In organic chemistry, a directing group (DG) is a substituent on a molecule or ion that facilitates reactions by interacting with a reagent. The term is usually applied to C-H activation of hydrocarbons, where it is defined as a "coordinating moiety (an “internal ligand”), which directs a metal catalyst into the proximity of a certain C–H bond." In a well known example, the ketone group () in acetophenone is the DG in the Murai reaction. The Murai reaction is related to directed ortho metalation, a reaction is typically applied to the lithiation of substituted aromatic rings.''Directed ortho metalation. Tertiary amide and O-carbamate directors in synthetic strategies for polysubstituted aromatics Victor Snieckus'' Chem. Rev.; 1990; 90(6); 879-933Abstract/ref> A wide variety of functional groups can serve as directing groups. Transient directing groups Since directing groups are ligands, their effectiveness correlates with their affinities for metals. Common fun ...
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Organic Chemistry
Organic chemistry is a subdiscipline within chemistry 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.Clayden, J.; Greeves, N. and Warren, S. (2012) ''Organic Chemistry''. Oxford University Press. pp. 1–15. . Study of structure determines their structural formula. Study of properties includes physical and chemical properties, and evaluation of chemical reactivity to understand their behavior. The study of organic reactions includes the chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and via theoretical ( in silico) study. The range of chemicals studied in organic chemistry includes hydrocarbons (compounds containing only carbon and hydrogen) as well as compounds based on carbon, but also containing other elements, especially oxygen, nitrogen, sulfur, phosphorus (included in ...
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Acetophenone
Acetophenone is the organic compound with the formula C6H5C(O)CH3. It is the simplest aromatic ketone. This colorless, viscous liquid is a precursor to useful resins and fragrances. Production Acetophenone is formed as a byproduct of the cumene process, the industrial route for the synthesis of phenol and acetone. In the Hock rearrangement of isopropylbenzene hydroperoxide, migration of a methyl group rather than the phenyl group gives acetophenone and methanol as a result of an alternate rearrangement of the intermediate: :C6H5C(CH3)2O2H -> C6H5C(O)CH3 + CH3OH The cumene process is conducted on such a large scale that even the small amount of acetophenone by-product can be recovered in commercially useful quantities. Acetophenone is also generated from ethylbenzene hydroperoxide. Ethylbenzene hydroperoxide is primarily converted to 1-phenylethanol (α-methylbenzyl alcohol) in the process with a small amount of by-product acetophenone. Acetophenone is recovered or hydrogena ...
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Schiff Base
In organic chemistry, a Schiff base (named after Hugo Schiff) is a compound with the general structure ( = alkyl or aryl, but not hydrogen). They can be considered a sub-class of imines, being either secondary ketimines or secondary aldimines depending on their structure. The term is often synonymous with azomethine which refers specifically to secondary aldimines (i.e. where R' ≠ H). A number of special naming systems exist for these compounds. For instance a Schiff base derived from an aniline, where is a phenyl or a substituted phenyl, can be called an ''anil'', while bis-compounds are often referred to as salen-type compounds. The term Schiff base is normally applied to these compounds when they are being used as ligands to form coordination complexes with metal ions. Such complexes occur naturally, for instance in corrin, but the majority of Schiff bases are artificial and are used to form many important catalysts, such as Jacobsen's catalyst. Synthesis Schiff ...
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Functional Group
In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The reactivity of a functional group can be modified by other functional groups nearby. Functional group interconversion can be used in retrosynthetic analysis to plan organic synthesis. A functional group is a group of atoms in a molecule with distinctive chemical properties, regardless of the other atoms in the molecule. The atoms in a functional group are linked to each other and to the rest of the molecule by covalent bonds. For repeating units of polymers, functional groups attach to their nonpolar core of carbon atoms and thus add chemical character to carbon chains. Fun ...
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Chem
Chem may refer to: * Chemistry practical waali mam *Chemistry *Chemical * ''Chem'' (journal), a scientific journal published by Cell Press *Post apocalyptic slang for "drugs", medicinal or otherwise in the Fallout video game series. In Ancient Egyptian usage: * ''Khem'' (also spelt ''Chem''), the Egyptian word for "black" * Min (god), in the past erroneously named ''Khem'' CHEM may refer to : *A metabolic panel: for instance, CHEM-7, which is the basic metabolic panel *CHEM-DT CHEM-DT is the TVA owned-and-operated television station in Trois-Rivières, Quebec, Canada. It broadcasts a high-definition digital signal on VHF channel 8 from a transmitter on Rue Principale in Notre-Dame-du-Mont-Carmel. Owned by the Grou ..., a Canadian television channel See also * Chemo (other) * Kemi, a place in Finland {{disambig ...
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Lithiation
In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium Lithium (from el, λίθος, lithos, lit=stone) is a chemical element with the 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 el ... (C–Li) Chemical bond, 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 ionization, ionic. Owing to the polar nat ...
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Directed Ortho Metalation
Directed ortho metalation (DoM) is an adaptation of electrophilic aromatic substitution in which electrophiles attach themselves exclusively to the ortho- position of a direct metalation group or DMG through the intermediary of an aryllithium compound. The DMG interacts with lithium through a hetero atom. Examples of DMG's are the methoxy group, a tertiary amine group and an amide group.The compound can be produced by directed lithiation of anisole. The general principle is outlined in ''scheme 1''. An aromatic ring system with a DMG group 1 interacts with an alkyllithium such as ''n''-butyllithium in its specific aggregation state (hence (R-Li)n) to intermediate 2 since the hetero atom on the DMG is a Lewis base and lithium the Lewis acid. The very basic alkyllithium then deprotonates the ring in the nearest ortho- position forming the aryllithium 3 all the while maintaining the acid-base interaction. An electrophile reacts in the next phase in an electrophilic aromatic subs ...
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Figure 1
Figure 1 is a Toronto, Ontario-based online social networking service for healthcare professionals to post and comment on medical images. Figure 1 was founded in Toronto by Dr. Joshua Landy, Richard Penner and Gregory Levey. The platform launched in North America in May 2013 and is now available in more than 100 countries. The privately held company reports more than 1 million healthcare professionals use its app and website. Funding In 2013, Figure 1 launched with $2 million (CDN) in seed money, with Rho Canada Ventures and Version One Ventures led the investment. In 2015, the company added $5 million (USD) to its Series A financing round, which was led by Union Square Ventures, an early investor in Twitter, Tumblr, Etsy, and Kickstarter. This brings the total round to $9 million (USD). Reception Figure 1's content has been characterized as "gruesome". The app's founder said the "very colorful images" are what medics see every day. "It's a transparent view into a world y ...
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Murai Reaction
In organic chemistry, the Murai reaction is an organic reaction that uses C-H activation to create a new C-C bond between a terminal or strained internal alkene and an aromatic compound using a ruthenium catalyst. The reaction, named after Shinji Murai, was first reported in 1993. While not the first example of C-H activation, the Murai reaction is notable for its high efficiency and scope. Previous examples of such hydroarylations required more forcing conditions and narrow scope. Scope and regiochemistry The reaction was initially demonstrated using a ketone as the directing group, but other functional groups have been reported, including esters, imines, nitriles, and imidates. Murai reactions have also been reported with disubstituted alkynes. bidentate directing group allow ''ortho'' alkylation of aromatic rings with α,β-unsaturated ketones, which typically are unreactive in Murai reactions. Early examples of the reaction suffered from side products of alkylation at bo ...
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Ketone
In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bond C=O). The simplest ketone is acetone (where R and R' is methyl), with the formula . Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids (e.g., testosterone), and the solvent acetone. Nomenclature and etymology The word ''ketone'' is derived from ''Aketon'', an old German word for ''acetone''. According to the rules of IUPAC nomenclature, ketone names are derived by changing the suffix ''-ane'' of the parent alkane to ''-anone''. Typically, the position of the carbonyl group is denoted by a number, but traditional nonsystematic names are still generally used for the most important ketones, for example acetone and benzophenone. These nonsystematic names are considere ...
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Substituent
A substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. (In organic chemistry and biochemistry, the terms ''substituent'' and ''functional group'', as well as ''side chain'' and '' pendant group'', are used almost interchangeably to describe those branches from the parent structure, though certain distinctions are made in polymer chemistry. In polymers, side chains extend from the backbone structure. In proteins, side chains are attached to the alpha carbon atoms of the amino acid backbone.) The suffix ''-yl'' is used when naming organic compounds that contain a single bond replacing one hydrogen; ''-ylidene'' and ''-ylidyne'' are used with double bonds and triple bonds, respectively. In addition, when naming hydrocarbons that contain a substituent, positional numbers are used to indicate which carbon atom the substituent attaches to when such information is needed to distinguish between isomers. Su ...
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