A metal-centered cycloaddition is a subtype of the more general class of cycloaddition reactions. In such reactions "two or more unsaturated molecules...
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diene. Other cycloaddition reactions exist: (4+3) cycloadditions, [6+4] cycloadditions, [2 + 2] photocycloadditions, metal-centered cycloaddition and [4+4]...
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olefins and elimination side reactions. Some success has been found with non-metal-catalyzed cycloadditions, such as the reactions using dipolarophiles that...
21 KB (2,639 words) - 20:31, 22 July 2024
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 (6,396 words) - 07:16, 24 May 2025
Metal-catalyzed cyclopropanations are chemical reactions that result in the formation of a cyclopropane ring from a metal carbenoid species and an alkene...
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of a pericyclic reaction with a concerted mechanism. More specifically, it is classified as a thermally allowed [4+2] cycloaddition with Woodward–Hoffmann...
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Click chemistry (redirect from Click reaction)
use of "click reactions", a set of simple, biocompatible chemical reactions that meet specific criteria like high yield, fast reaction rates, and minimal...
48 KB (5,449 words) - 15:24, 15 June 2025
sigmatropic reaction such as the Cope rearrangement. Cyclic rearrangements include cycloadditions and, more generally, pericyclic reactions, wherein two...
66 KB (8,057 words) - 01:14, 16 June 2025
Alkene (section Cycloaddition)
via rearrangement reactions. Besides olefin metathesis (described above), many pericyclic reactions can be used such as the ene reaction and the Cope rearrangement...
49 KB (5,266 words) - 15:49, 29 May 2025
Desulfonylation reactions are chemical reactions leading to the removal of a sulfonyl group from organic compounds. As the sulfonyl functional group is...
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provide the other coupling partner. The Stille reaction is one of many palladium-catalyzed coupling reactions. R 1 − Sn ( Alkyl ) 3 + R 2 − X → ligand set...
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Photoredox catalysis (section Cycloadditions)
undergo intramolecular radical-anion hetero-Diels–Alder reactions more rapidly than [2+2] cycloaddition. Similarly, electron-rich styrenes participate in intra-...
50 KB (6,257 words) - 20:42, 12 June 2025
1021/cr950015t. PMID 11848759. Welker, Mark E. (1992). "3 + 2 Cycloaddition reactions of transition-metal 2-alkynyl and .eta.1-allyl complexes and their utilization...
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complexes: Versatile catalysts for enantioselective cycloaddition, Aldol, Michael, and carbonyl ene reactions". Acc. Chem. Res. 33 (6): 325–35. doi:10.1021/ar960062n...
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as nucleophilic partners in cross-coupling reactions. Typically, nucleophilic reagents in coupling reactions tend to be of the organometallic variety,...
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Chiral auxiliary (section Alkylation reactions)
Chapman, K. T.; Bisaha, J. (1984). "New Asymmetric Diels-Alder Cycloaddition Reactions. Chiral α,β-Unsaturated Carboximides as Practical Chiral Acrylate...
34 KB (3,726 words) - 10:21, 15 March 2025
Lewis acid catalysis (category Chemical reactions)
attack, heterolytic bond cleavage, or cycloaddition with 1,3-dienes and 1,3-dipoles. Many classical reactions involving carbon–carbon or carbon–heteroatom...
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with one triazole unit bridging two metal centers, and is an effective catalyst for the 'click' cycloaddition reaction. The structure of the complex of TBTA...
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cyclization reactions and Diels-Alder reactions. The weakly coordinating nature of the THF ligand in W(CO)5(THF) renders the tungsten center a potent Lewis...
33 KB (3,002 words) - 13:57, 22 May 2025
products. Cycloadditions can occur on metal vinylidenes at either the M=Cα or Cα=Cβ bonds. These can serve in both [2+2] and [4+2] cycloadditions with a...
15 KB (1,519 words) - 20:28, 16 June 2025
Bioorthogonal chemistry (category Biochemical reactions)
thermodynamics and kinetics of these cycloaddition reactions which has played a vital role in continuing to improve the reaction. There are two methods for activating...
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Pyridine (redirect from Emmert reaction)
activation requires high pressures and temperatures, the photoinduced cycloaddition proceeds at ambient conditions with CoCp2(cod) (Cp = cyclopentadienyl...
77 KB (7,673 words) - 01:52, 30 May 2025
Digermyne (section Cycloaddition)
different kinds of reactions, such as [2+1] and [2+2] cycloaddition reaction with different kinds of unsaturated molecules, [4+1] cycloaddition with 1,3-dimethyl-1...
20 KB (2,507 words) - 05:51, 28 November 2024
Phosphetane (section [2+2] cycloaddition)
chemical reaction, cases where phosphetanes are used as the active reagents in chemical reactions, and cases where phosphetanes are ligated to a metal that...
50 KB (5,139 words) - 14:51, 16 June 2025
efficiently has made this reaction particularly attractive synthetically. (1) The metal-free version of the [6+4] cycloaddition takes place through a concerted...
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arm largely losing coordination with the bismuth(III) center. A similar cycloaddition reaction between Dostál's bismuthinidene and methyl propiolate yields...
40 KB (4,489 words) - 01:11, 27 May 2025
Aldehyde (section Common reactions)
carbon dioxide. Aldehydes participate in many reactions. From the industrial perspective, important reactions are: condensations, e.g., to prepare plasticizers...
30 KB (3,112 words) - 13:18, 1 June 2025
Topochemical polymerization (category Polymerization reactions)
prepare. Various reactions have been adopted in the field of topochemical polymerisation, such as [2+2], [4+2], [4+4], and [3+2] cycloaddition, linear addition...
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Captodative effect (category Chemical reactions)
The term "captodative ethylenes" has been used in the context of cycloaddition reactions involving captodative radical intermediates – for example, the...
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4+4 Photocycloaddition (category Cycloadditions)
The [4+4] Photocycloaddition is a cycloaddition reaction in which two unsaturated molecules connect via four atoms from each molecule (hence "4 + 4") to...
8 KB (917 words) - 11:57, 13 August 2023