• Thumbnail for Cycloaddition
    In organic chemistry, a cycloaddition is a chemical reaction in which "two or more unsaturated molecules (or parts of the same molecule) combine with...
    12 KB (1,322 words) - 08:28, 6 July 2025
  • 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...
    65 KB (6,458 words) - 13:19, 24 June 2025
  • 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...
    21 KB (2,656 words) - 13:27, 24 June 2025
  • fulfill the requirements of bioorthogonality, including the 1,3-dipolar cycloaddition between azides and cyclooctynes (also termed copper-free click chemistry)...
    44 KB (5,126 words) - 02:25, 28 June 2025
  • Thumbnail for Diels–Alder 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...
    48 KB (5,449 words) - 23:45, 1 August 2025
  • Thumbnail for Ketene
    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...
    15 KB (1,702 words) - 21:41, 30 June 2025
  • Thumbnail for Azomethine ylide
    of an iminium ion next to a carbanion. They are used in 1,3-dipolar cycloaddition reactions to form five-membered heterocycles, including pyrrolidines...
    18 KB (1,988 words) - 01:46, 19 April 2024
  • cycloaddition reaction is the combination of a nitrone with an alkene or alkyne to generate an isoxazoline or isoxazolidine via a (3+2) cycloaddition...
    7 KB (923 words) - 22:24, 27 September 2024
  • Thumbnail for Woodward–Hoffmann rules
    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...
    89 KB (11,215 words) - 18:08, 3 August 2025
  • Thumbnail for Alkyne
    specialized cycloadditions include multicomponent reactions such as alkyne trimerisation to give aromatic compounds and the [2+2+1]-cycloaddition of an alkyne...
    24 KB (3,193 words) - 03:32, 16 June 2025
  • Thumbnail for Pericyclic reaction
    cheletropic reactions are often classed as group transfer reactions and cycloadditions/cycloeliminations, respectively, while dyotropic reactions and group...
    10 KB (1,162 words) - 16:49, 21 April 2024
  • In organic chemistry, enone–alkene cycloadditions are a version of the [2+2] cycloaddition. This reaction involves an enone and alkene as substrates....
    9 KB (1,040 words) - 13:44, 24 June 2025
  • 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...
    18 KB (1,954 words) - 13:24, 24 June 2025
  • hydrolysis with Mercury(II) chloride in water. Thiazoles can react in cycloadditions, but in general at high temperatures due to favorable aromatic stabilization...
    12 KB (1,151 words) - 16:39, 22 July 2025
  • A metal-centered cycloaddition is a subtype of the more general class of cycloaddition reactions. In such reactions "two or more unsaturated molecules...
    10 KB (1,042 words) - 02:05, 20 July 2025
  • 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...
    1 KB (119 words) - 13:28, 24 June 2025
  • Thumbnail for Nitrone
    intermediates in chemical synthesis. A nitrone is a 1,3-dipole used in cycloadditions, and a carbonyl mimic. Nitrones, as a tetrasubstituted double bond,...
    6 KB (493 words) - 15:06, 21 May 2025
  • Thumbnail for Chemical reaction
    molecule. An important example of cycloaddition reaction is the Diels–Alder reaction (the so-called [4+2] cycloaddition) between a conjugated diene and...
    66 KB (8,048 words) - 01:14, 16 June 2025
  • Thumbnail for Photoredox catalysis
    (FMO) or the Dewar-Zimmermann model. Cycloadditions that are not thermally allowed, such as the [2+2] cycloaddition, can be enabled by photochemical activation...
    50 KB (6,259 words) - 11:09, 30 June 2025
  • Thumbnail for Rolf Huisgen
    achievement was the development of the 1,3-dipolar cycloaddition reaction, also called the Huisgen cycloaddition. Huisgen was born in Gerolstein in Rhineland-Palatinate...
    9 KB (713 words) - 15:34, 24 May 2025
  • Curtius rearrangement. Rolf Huisgen described the eponymous 1,3-dipolar cycloaddition. The interest in azides among organic chemists has been relatively modest...
    28 KB (2,857 words) - 10:40, 18 July 2025
  • 14. Gold-catalyzed formal intramolecular [4+2] cycloaddition of 1,6-enynes This formal cycloaddition was proposed to proceed via the cascade process...
    26 KB (2,852 words) - 18:17, 27 May 2025
  • Thumbnail for Digermyne
    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...
    20 KB (2,507 words) - 05:51, 28 November 2024
  • 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...
    2 KB (266 words) - 18:45, 28 July 2016
  • Thumbnail for Wolff rearrangement
    and amines, to generate carboxylic acid derivatives or undergo [2+2] cycloaddition reactions to form four-membered rings. The mechanism of the Wolff rearrangement...
    36 KB (4,578 words) - 06:29, 30 July 2025
  • 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...
    10 KB (1,151 words) - 16:23, 23 June 2025
  • is a bioorthogonal reaction as a variant of an azide-alkyne Huisgen cycloaddition. By eliminating cytotoxic copper catalysts, the reaction proceeds without...
    7 KB (878 words) - 17:17, 28 May 2025
  • 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...
    10 KB (1,343 words) - 18:11, 14 December 2024
  • Thumbnail for On-water reaction
    Enhanced reactivity is also found in cycloadditions. The reaction of quadricyclane with DEAD is a 2σ + 2σ + 2π cycloaddition that on water takes place within...
    6 KB (784 words) - 06:12, 5 February 2025