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Annulation

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In organic chemistry, annulation (from Latin anellus'little ring'; occasionally annelation) is a chemical reaction in which a new ring is constructed on a molecule. Examples are the Robinson annulation, Danheiser annulation and certain cycloadditions. Annular molecules are constructed from side-on condensed cyclic segments, for example helicenes and acenes. TransannulationIn transannulation a bicyclic molecule is created by intramolecularcarbon-carbon bond formation in a large monocyclic ring.

Intramolecular reactionIntramolecular reactionIn chemistry, intramolecular describes a process or characteristic limited within the structure of a single molecule, a property or phenomenon limited to the extent of a single molecule. Relative ratesIn intramolecular organic reactions, two reaction sites are contained within a single molecule. This configuration elevates the effective concentration of the reacting partners resulting in high reaction rates.Chemical reactionChemical reactionProcess that leads to chemical changesA thermite reaction using iron(III) oxide. The sparks flying outwards are globules of molten iron trailing smoke in their wake.A chemical reaction is a process that leads to the chemical transformation of one set of chemical substances to another. When chemical reactions occur, the atoms are rearranged and the reaction is accompanied by an energy change as new products are generated.Organic chemistryOrganic chemistryOrganic 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 carbonatoms). It involves studying the structure of organic material to determine the structural formula, analyzing physical and chemical properties, and evaluating chemical reactivity to understand the behavior of organic compounds.Danheiser annulationDanheiser annulationThe Danheiser annulation or Danheiser TMS-cyclopentene annulation is an organic reaction of an α,β-unsaturated ketone and a trialkylsilylallene (e.g., trimethylsilyl- or triisopropylsilyl-) in the presence of a Lewis Acid to give a trialkylsilylcyclopentene in a regiocontrolled annulation.Robinson annulationThe Robinson annulation is a chemical reaction used in organic chemistry for ring formation. It was discovered by Robert Robinson in 1935 as a method to create a six membered ring by forming three new carbon–carbon bonds. The method uses a ketone and a methyl vinyl ketone to form an α,β-unsaturated ketone in a cyclohexane ring by a Michael addition followed by an aldol condensation. This procedure is one of the key methods to form fused ring systems.KetoneKetoneIn organic chemistry, a ketone is an organic compound 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)− (a carbon-oxygen double bond C=O). A ketone derived from an alkane is an alkanone. The simplest ketone is acetone (where R and R' are methyl), with the formula (CH3)2CO. Many ketones are of great importance in biology and industry.Samarium(II) iodideSamarium(II) iodideSamarium(II) iodide is an inorganic compound with the formula SmI2. When employed as a solution for organic synthesis, it is known as Kagan's reagent, named after Henri B. Kagan. SmI2 is a green solid and forms a dark blue solution in THF. It is a strong one-electron reducing agent that is used in organic synthesis. StructureIn solid samarium(II) iodide, the metal centers are seven-coordinate with a face-capped octahedral geometry.Ring (chemistry)Ring (chemistry)In chemistry, a ring is an ambiguous term referring either to a simple of atoms and bonds in a molecule or to a connected set of atoms and bonds in which every atom and bond is a member of a cycle (also called a ring system). A ring system that is a simple cycle is called a monocycle or simple ring, and one that is not a simple cycle is called a polycycle or polycyclic ring system.CycloadditionCycloadditionIn organic chemistry, a cycloaddition is a chemical reaction in which "two or more 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 bond multiplicity". The resulting reaction is a cyclization reaction. Many but not all cycloadditions are concerted and thus pericyclic. Nonconcerted cycloadditions are not pericyclic.HeliceneHeliceneIn organic chemistry, helicenes are ortho-condensed polycyclic aromatic compounds in which benzene rings or other aromatics are angularly annulated to give helically-shaped chiral molecules. The chemistry of helicenes has attracted continuing attention because of their unique structural, spectral, and optical features.AceneAceneIn organic chemistry, the acenes or polyacenes are a class of organic compounds and polycyclic aromatic hydrocarbons made up of benzene (C6H6) rings which have been linearly fused. They follow the general molecular formulaC4n+2H2n+4. The larger representatives have potential interest in optoelectronic applications and are actively researched in chemistry and electrical engineering.Bicyclic moleculeBicyclic moleculeA bicyclic molecule (from bi'two' and cycle'ring') is a molecule that features two joined rings. Bicyclic structures occur widely, for example in many biologically important molecules like α-thujene and camphor. A bicyclic compound can be carbocyclic (all of the ring atoms are carbons), or heterocyclic (the rings' atoms consist of at least two elements), like DABCO.

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