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Dearomatization
A dearomatization reaction is an organic reaction which involves arenes as reactants and in which the reaction products have permanently lost their aromaticity. This reaction type is of some importance in synthetic organic chemistry for the organic synthesis of new building blocks and in total synthesis. Several methods for the dearomatization of carbocyclic arenes exist: hydrogenation (Birch reduction), alkylative dearomatization, photochemical dearomatization, thermal dearomatization, oxidative dearomatization, dearomatization with transition metals and enzymatic dearomatization. Photochemical dearomatization Examples of photochemical reactions are those between certain arenes and alkenes forming +2and +4cycloaddition adducts. Enzymatic dearomatization Examples of enzymes capable of arene dearomatization are toluene dixoyhydrogenase, naphthalene dixoyhydrogenase and benzoyl CoA reductase. Transition-metal assisted dearomatization A classic example of transition-metal assis ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Aromatic Hydrocarbon
Aromatic compounds, also known as "mono- and polycyclic aromatic hydrocarbons", are organic compounds containing one or more aromatic rings. The parent member of aromatic compounds is benzene. The word "aromatic" originates from the past grouping of molecules based on smell, before their general chemical properties are understood. The current definition of aromatic compounds does not have any relation with their smell. Heteroarenes are closely related, since at least one carbon atom of CH group is replaced by one of the heteroatoms oxygen, nitrogen, or sulfur. Examples of non-benzene compounds with aromatic properties are furan, a heterocyclic compound with a five-membered ring that includes a single oxygen atom, and pyridine, a heterocyclic compound with a six-membered ring containing one nitrogen atom. Hydrocarbons without an aromatic ring are called aliphatic. Benzene ring model Benzene, C6H6, is the least complex aromatic hydrocarbon, and it was the first one named as such ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organic Reaction
Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions, Mechanistic Organic Photochemistry, photochemical reactions and organic redox reaction, redox reactions. In organic synthesis, organic reactions are used in the construction of new organic molecules. The production of many man-made chemicals such as drugs, plastics, food additives, fabrics depend on organic reactions. The oldest organic reactions are combustion of organic fuels and saponification of fats to make soap. Modern organic chemistry starts with the Wöhler synthesis in 1828. In the history of the Nobel Prize in Chemistry awards have been given for the invention of specific organic reactions such as the Grignard reaction in 1912, the Diels-Alder reaction in 1950, the Wittig reaction in 1979 and olefin metathesis in 2005. Classifications Organic c ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Aromaticity
In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to saturated compounds having single bonds, and other geometric or connective non-cyclic arrangements with the same set of atoms. Aromatic rings are very stable and do not break apart easily. Organic compounds that are not aromatic are classified as aliphatic compounds—they might be cyclic, but only aromatic rings have enhanced stability. The term ''aromaticity'' with this meaning is historically related to the concept of having an aroma, but is a distinct property from that meaning. Since the most common aromatic compounds are derivatives of benzene (an aromatic hydrocarbon common in petroleum and its distillates), the word ''aromatic'' occasionally refers informally to benzene derivatives, and so it was first defined. Nevertheless, many non-be ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Total Synthesis
Total synthesis is the complete chemical synthesis of a complex molecule, often a natural product, from simple, commercially-available precursors. It usually refers to a process not involving the aid of biological processes, which distinguishes it from semisynthesis. Syntheses may sometimes conclude at a precursor with further known synthetic pathways to a target molecule, in which case it is known as a formal synthesis. Total synthesis target molecules can be natural products, medicinally-important active ingredients, known intermediates, or molecules of theoretical interest. Total synthesis targets can also be organometallic or inorganic, though these are rarely encountered. Total synthesis projects often require a wide diversity of reactions and reagents, and subsequently requires broad chemical knowledge and training to be successful. Often, the aim is to discover a new route of synthesis for a target molecule for which there already exist known routes. Sometimes, however, no ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Birch Reduction
The Birch reduction is an organic reaction that is used to convert arenes to cyclohexadienes. The reaction is named after the Australian chemist Arthur Birch and involves the organic reduction of aromatic rings in an amine solvent (traditionally liquid ammonia) with an alkali metal (traditionally sodium) and a proton source (traditionally an alcohol). Unlike catalytic hydrogenation, Birch reduction does not reduce the aromatic ring all the way to a cyclohexane. An example is the reduction of naphthalene in ammonia and ethanol: Reaction mechanism and regioselectivity A solution of sodium in liquid ammonia consists of the intensely blue electride salt a(NH3)xsup>+ e−. The solvated electrons add to the aromatic ring to give a radical anion, which then abstracts a proton from the alcohol. The process then repeats at either the ''ortho'' or ''para'' position (depending on substituents) to give the final diene. The residual double bonds do not stabilize further radical add ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Cycloaddition
In organic chemistry, a cycloaddition is a chemical reaction in which "two or more Unsaturated hydrocarbon, unsaturated molecules (or parts of the same molecule) combine with the formation of a cyclic adduct in which there is a net reduction of the Multiplicity (chemistry)#Molecules, bond multiplicity". The resulting reaction is a cyclization reaction. Many but not all cycloadditions are Concerted reaction, concerted and thus pericyclic. Nonconcerted cycloadditions are not pericyclic. As a class of addition reaction, cycloadditions permit carbon–carbon bond formation without the use of a nucleophile or electrophile. Cycloadditions can be described using two systems of notation. An older but still common notation is based on the size of linear arrangements of atoms in the reactants. It uses parentheses: where the variables are the numbers of linear atoms in each reactant. The product is a cycle of size . In this system, the standard Diels-Alder reaction is a (4 + 2)-cyc ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Buchner Ring Expansion
The Buchner ring expansion is a two-step organic C-C bond forming reaction used to access 7-membered rings. The first step involves formation of a carbene from ethyl diazoacetate, which cyclopropanates an aromatic ring. The ring expansion occurs in the second step, with an electrocyclic reaction opening the cyclopropane ring to form the 7-membered ring. History The Buchner ring expansion reaction was first used in 1885 by E. Buchner and T. Curtius who prepared a carbene from ethyl diazoacetate for addition to benzene using both thermal and photochemical pathways in the synthesis of cycloheptatriene derivatives. The resulting product was a mixture of four isomeric carboxylic acids. Variations in the reaction arise from methods of carbene preparation. Advances in organometallic chemistry have resulted in increased selectivity of cycloheptatriene derivatives. In the 1980s it was found that dirhodium catalysts provide single cyclopropane isomers in high yields. Applicatio ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Enantioselective Synthesis
Enantioselective synthesis, also called asymmetric synthesis, is a form of chemical synthesis. It is defined by IUPAC as "a chemical reaction (or reaction sequence) in which one or more new elements of chirality are formed in a substrate molecule and which produces the stereoisomeric (enantiomeric or diastereomeric) products in unequal amounts." Put more simply: it is the synthesis of a compound by a method that favors the formation of a specific enantiomer or diastereomer. Enantiomers are stereoisomers that have opposite configurations at every chiral center. Diastereomers are stereoisomers that differ at one or more chiral centers. Enantioselective synthesis is a key process in modern chemistry and is particularly important in the field of pharmaceuticals, as the different enantiomers or diastereomers of a molecule often have different biological activity. Overview Many of the building blocks of biological systems such as sugars and amino acids are produced exclusively as ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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