In organic chemistry, a cycloaddition is a chemical reaction in which "two or more unsaturated molecules (or parts of the same molecule) combine with...
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cycloaddition is a chemical reaction between a 1,3-dipole and a dipolarophile to form a five-membered ring. The earliest 1,3-dipolar cycloadditions were...
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The azide-alkyne Huisgen cycloaddition is a 1,3-dipolar cycloaddition between an azide and a terminal or internal alkyne to give a 1,2,3-triazole. Rolf...
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fulfill the requirements of bioorthogonality, including the 1,3-dipolar cycloaddition between azides and cyclooctynes (also termed copper-free click chemistry)...
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Diels–Alder reaction (redirect from Diels-Alder cycloaddition reaction)
mechanism. More specifically, it is classified as a thermally allowed [4+2] cycloaddition with Woodward–Hoffmann symbol [π4s + π2s]. It was first described by...
70 KB (8,039 words) - 01:56, 30 July 2025
better than others:[clarification needed] [3+2] cycloadditions, such as the Huisgen 1,3-dipolar cycloaddition, in particular the Cu(I)-catalyzed stepwise...
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Ketene (redirect from Ketene cycloaddition)
to cycloaddition products in high enantiomeric excess. In rarer cases, ketenes may undergo [3+2], and [4+2] cycloadditions. [3+2] Cycloadditions may...
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of an iminium ion next to a carbanion. They are used in 1,3-dipolar cycloaddition reactions to form five-membered heterocycles, including pyrrolidines...
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cycloaddition reaction is the combination of a nitrone with an alkene or alkyne to generate an isoxazoline or isoxazolidine via a (3+2) cycloaddition...
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Woodward–Hoffmann rules (redirect from 2+2 Cycloaddition)
formidable (up to ca. 5 eV or 480 kJ/mol in the case of a forbidden [2+2] cycloaddition), the prohibition is not absolute, and symmetry-forbidden reactions...
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In organic chemistry, enone–alkene cycloadditions are a version of the [2+2] cycloaddition. This reaction involves an enone and alkene as substrates....
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Photoredox catalysis (section Cycloadditions)
(FMO) or the Dewar-Zimmermann model. Cycloadditions that are not thermally allowed, such as the [2+2] cycloaddition, can be enabled by photochemical activation...
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Alkyne (section Cycloadditions and oxidation)
specialized cycloadditions include multicomponent reactions such as alkyne trimerisation to give aromatic compounds and the [2+2+1]-cycloaddition of an alkyne...
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cheletropic reactions are often classed as group transfer reactions and cycloadditions/cycloeliminations, respectively, while dyotropic reactions and group...
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Alkyne trimerisation (category Cycloadditions)
An alkyne trimerisation is a [2+2+2] cycloaddition reaction in which three alkyne units (C≡C) react to form a benzene ring. The reaction requires a metal...
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hydrolysis with Mercury(II) chloride in water. Thiazoles can react in cycloadditions, but in general at high temperatures due to favorable aromatic stabilization...
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The Bradsher cycloaddition reaction, also known as the Bradsher cyclization reaction is a form of the Diels–Alder reaction which involves the [4+2] addition...
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Nitrone (section 1,3-dipolar cycloadditions)
intermediates in chemical synthesis. A nitrone is a 1,3-dipole used in cycloadditions, and a carbonyl mimic. Nitrones, as a tetrasubstituted double bond,...
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achievement was the development of the 1,3-dipolar cycloaddition reaction, also called the Huisgen cycloaddition. Huisgen was born in Gerolstein in Rhineland-Palatinate...
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Curtius rearrangement. Rolf Huisgen described the eponymous 1,3-dipolar cycloaddition. The interest in azides among organic chemists has been relatively modest...
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Wolff rearrangement (section Cycloaddition reactions)
and amines, to generate carboxylic acid derivatives or undergo [2+2] cycloaddition reactions to form four-membered rings. The mechanism of the Wolff rearrangement...
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14. Gold-catalyzed formal intramolecular [4+2] cycloaddition of 1,6-enynes This formal cycloaddition was proposed to proceed via the cascade process...
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Digermyne (section Cycloaddition)
reactions, such as [2+1] and [2+2] cycloaddition reaction with different kinds of unsaturated molecules, [4+1] cycloaddition with 1,3-dimethyl-1,3-butadiene...
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is a bioorthogonal reaction as a variant of an azide-alkyne Huisgen cycloaddition. By eliminating cytotoxic copper catalysts, the reaction proceeds without...
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The Boger pyridine synthesis is a cycloaddition approach to the formation of pyridines named after its inventor Dale L. Boger, who first reported it in...
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Ylide (section Dipolar cycloadditions)
there are more. Some ylides are 1,3-dipoles and interact in 1,3-dipolar cycloadditions. For instance an azomethine ylide is a dipole in the Prato reaction...
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number of these systems is odd then the reaction is thermally allowed. A cycloaddition is a reaction that simultaneously forms at least two new bonds, and...
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molecule. An important example of cycloaddition reaction is the Diels–Alder reaction (the so-called [4+2] cycloaddition) between a conjugated diene and...
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Alkylidene ketene (section Cycloaddition)
pressure. Alkylidene ketenes can readily dimerize and participate in cycloaddition reactions. Often orange or red in color, these dimers can be generated...
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Vinylcyclopropane (5+2) cycloaddition is a type of cycloaddition between a vinylcyclopropane (VCP) and an olefin or alkyne to form a seven-membered ring...
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