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Fráter–Seebach Alkylation
In organic chemistry, the Fráter–Seebach alkylation (also known as Seebach–Fráter alkylation or Fráter–Seebach reaction) is a diastereoselective alkylation of chiral beta-hydroxy esters using strong base (chemistry), bases. The reaction was first published by Georg Fráter in 1979; in 1980, Dieter Seebach reported about a similar reaction with malic acid ester. Outline and mechanism Chiral beta-hydroxy esters can be treated with two equivalents of a strong base (lithium diisopropylamide, lithium diisopropylamide (LDA) or Lithium bis(trimethylsilyl)amide, lithium bis(trimethylsilyl)amide (LHMDS) are popular choices) to both remove the proton on the alcohol and Enolization, enolize the ester. An alkylating agent (methyl iodide in the case of Fráter's publication) is then added. This attacks from the opposite face of the chiral hydroxyl group to avoid steric hindrance as shown below in the 6-membered transition state with Chelation, chelating metal ions. This reaction has ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Outline Of Fráter–Seebach Alkylation
Outline or outlining may refer to: * Outline (list), a document summary, in hierarchical list format * Code folding, a method of hiding or collapsing code or text to see content in outline form * Outline drawing, a sketch depicting the outer edges of a person or object, without interior details or shading * Outline (note-taking software), a note-taking application * Outline typeface, in typography * Outline VPN, a free and open-source Shadowsocks deployment tool * Outline, the representation of a word in shorthand * Step outline, or just outline, the first summary of a story for a film script Media * ''Outline'' (novel), a 2014 novel by Rachel Cusk * ''Outlines'' (collection), a 1939 collection of poems by surrealist poet Jean Venturini * The Outline (website), a news company * Outlines Festival, an annual one-day music festival held in Sheffield, United Kingdom * Outline Records, record label founded by Jane Ira Bloom * The Outline (band), an experimental band from the United S ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
John Wiley & Sons
John Wiley & Sons, Inc., commonly known as Wiley (), is an American multinational publishing company founded in 1807 that focuses on academic publishing and instructional materials. The company produces books, journals, and encyclopedias, in print and electronically, as well as online products and services, training materials, and educational materials for undergraduate, graduate, and continuing education students. History The company was established in 1807 when Charles Wiley opened a print shop in Manhattan. The company was the publisher of 19th century American literary figures like James Fenimore Cooper, Washington Irving, Herman Melville, and Edgar Allan Poe, as well as of legal, religious, and other non-fiction titles. The firm took its current name in 1865. Wiley later shifted its focus to scientific, technical, and engineering subject areas, abandoning its literary interests. Wiley's son John (born in Flatbush, New York, October 4, 1808; died in East Orange, New Je ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Chelation
Chelation is a type of bonding of ions and molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a Denticity, polydentate (multiple bonded) ligand and a single central metal atom. These ligands are called chelants, chelators, chelating agents, or sequestering agents. They are usually organic compounds, but this is not a necessity, as in the case of zinc and its use as a maintenance therapy to prevent the absorption of copper in people with Wilson's disease. Chelation is useful in applications such as providing nutritional supplements, in chelation therapy to remove toxic metals from the body, as contrast medium, contrast agents in MRI, MRI scanning, in manufacturing using homogeneous catalysts, in chemical water treatment to assist in the removal of metals, and in fertilizers. Chelate effect The chelate effect is the greater affinity of chelating ligands for a metal ion than that of similar nonchelating (monodentate ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Transition State
In chemistry, the transition state of a chemical reaction is a particular configuration along the reaction coordinate. It is defined as the state corresponding to the highest potential energy along this reaction coordinate. It is often marked with the double dagger ‡ symbol. As an example, the transition state shown below occurs during the SN2 reaction of bromoethane with a hydroxide anion: The activated complex of a reaction can refer to either the transition state or to other states along the reaction coordinate between reactants and products, especially those close to the transition state.Peter Atkins and Julio de Paula, ''Physical Chemistry'' (8th ed., W.H. Freeman 2006), p.809 According to the transition state theory, once the reactants have passed through the transition state configuration, they always continue to form products. History of concept The concept of a transition state has been important in many theories of the rates at which chemical reactions occ ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Steric Hindrance
Steric effects arise from the spatial arrangement of atoms. When atoms come close together there is a rise in the energy of the molecule. Steric effects are nonbonding interactions that influence the shape ( conformation) and reactivity of ions and molecules. Steric effects complement electronic effects, which dictate the shape and reactivity of molecules. Steric repulsive forces between overlapping electron clouds result in structured groupings of molecules stabilized by the way that opposites attract and like charges repel. Steric hindrance Steric hindrance is a consequence of steric effects. Steric hindrance is the slowing of chemical reactions due to steric bulk. It is usually manifested in ''intermolecular reactions'', whereas discussion of steric effects often focus on ''intramolecular interactions''. Steric hindrance is often exploited to control selectivity, such as slowing unwanted side-reactions. Steric hindrance between adjacent groups can also affect torsional ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydroxyl
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy groups. Both the negatively charged anion , called hydroxide, and the neutral radical , known as the hydroxyl radical, consist of an unbonded hydroxy group. According to IUPAC definitions, the term ''hydroxyl'' refers to the hydroxyl radical () only, while the functional group is called a ''hydroxy group''. Properties Water, alcohols, carboxylic acids, and many other hydroxy-containing compounds can be readily deprotonated due to a large difference between the electronegativity of oxygen (3.5) and that of hydrogen (2.1). Hydroxy-containing compounds engage in intermolecular hydrogen bonding increasing the electrostatic attraction between molecules and thus to higher boiling and melting points than found for compounds that lack this f ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Methyl Iodide
Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one hydrogen atom by an atom of iodine. It is naturally emitted by rice plantations in small amounts. It is also produced in vast quantities estimated to be greater than 214,000 tons annually by algae and kelp in the world's temperate oceans, and in lesser amounts on land by terrestrial fungi and bacteria. It is used in organic synthesis as a source of methyl groups. Preparation and handling Iodomethane is formed via the exothermic reaction that occurs when iodine is added to a mixture of methanol with red phosphorus. The iodinating reagent is phosphorus triiodide that is formed ''in situ:'' :3 CH3OH + PI3 → 3 CH3I + H2PO3H Alternatively, it is prepared from the reaction of dimethyl sulfate with potassium iodide in the presence of ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Enolization
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 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Diastereoselective
In stereochemistry, diastereomers (sometimes called diastereoisomers) are a type of stereoisomer. Diastereomers are defined as non-mirror image, non-identical stereoisomers. Hence, they occur when two or more stereoisomers of a compound have different configurations at one or more (but not all) of the equivalent (related) stereocenters and are not mirror images of each other. When two diastereoisomers differ from each other at only one stereocenter, they are epimers. Each stereocenter gives rise to two different configurations and thus typically increases the number of stereoisomers by a factor of two. Diastereomers differ from enantiomers in that the latter are pairs of stereoisomers that differ in all stereocenters and are therefore mirror images of one another. Enantiomers of a compound with more than one stereocenter are also diastereomers of the other stereoisomers of that compound that are not their mirror image (that is, excluding the opposing enantiomer). Diastereomers h ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Lithium Bis(trimethylsilyl)amide
Lithium bis(trimethylsilyl)amide is a lithiated organosilicon compound with the formula . It is commonly abbreviated as LiHMDS or Li(HMDS) (lithium hexamethyldisilazide - a reference to its conjugate acid HMDS) and is primarily used as a strong non-nucleophilic base and as a ligand. Like many lithium reagents, it has a tendency to aggregate and will form a cyclic trimer in the absence of coordinating species. Preparation LiHMDS is commercially available, but it can also be prepared by the deprotonation of bis(trimethylsilyl)amine with ''n''-butyllithium. This reaction can be performed ''in situ''. : Once formed, the compound can be purified by sublimation or distillation. Reactions and applications As a base LiHMDS is often used in organic chemistry as a strong non-nucleophilic base. Its conjugate acid has a p''K''a of ~26, making it is less basic than other lithium bases, such as LDA (p''K''a of conjugate acid ~36), but it is more sterically hindered and hence less nu ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Lithium Diisopropylamide
Lithium diisopropylamide (commonly abbreviated LDA) is a chemical compound with the molecular formula . It is used as a strong base and has been widely utilized due to its good solubility in non-polar organic solvents and non-nucleophilic nature. It is a colorless solid, but is usually generated and observed only in solution. It was first prepared by Hamell and Levine in 1950 along with several other hindered lithium diorganylamides to effect the deprotonation of esters at the α position without attack of the carbonyl group. Preparation and structure LDA is commonly formed by treating a cooled (0 to −78 °C) mixture of tetrahydrofuran and diisopropylamine with ''n''-butyllithium. When dissociated, the diisopropylamide anion can become protonated to form diisopropylamine. Diisopropylamine has a p''K''a value of 36. Therefore, its conjugate base is suitable for the deprotonation of compounds with greater acidity, importantly, such weakly acidic compounds (carbon acids) ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
