• The 1,3-dipolar 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...
    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
  • Thumbnail for Cycloaddition
    (4 + 2)-cycloaddition, the 1,3-dipolar cycloaddition is a (3 + 2)-cycloaddition and cyclopropanation of a carbene with an alkene a (2 + 1)-cycloaddition. A...
    12 KB (1,322 words) - 08:28, 6 July 2025
  • a concerted [3+2] cycloaddition to the triple bond in a cyclooctyne in the same mechanism as the Huisgen 1,3-dipolar cycloaddition. Substituents other...
    48 KB (5,449 words) - 15:24, 15 June 2025
  • The Diazoalkane 1,3-dipolar cycloaddition is a 1,3-dipolar cycloaddition (an organic reaction) between a 1,3-dipole diazo compound (notably diazomethane)...
    2 KB (180 words) - 17:43, 10 November 2020
  • Thumbnail for Azomethine ylide
    ylides are nitrogen-based 1,3-dipoles, consisting of an iminium ion next to a carbanion. They are used in 1,3-dipolar cycloaddition reactions to form five-membered...
    18 KB (1,988 words) - 01:46, 19 April 2024
  • that fulfill the requirements of bioorthogonality, including the 1,3-dipolar cycloaddition between azides and cyclooctynes (also termed copper-free click...
    44 KB (5,126 words) - 02:25, 28 June 2025
  • cycloaddition process. This reaction is a 1,3-dipolar cycloaddition, in which the nitrone acts as the 1,3-dipole, and the alkene or alkyne as the dipolarophile...
    7 KB (923 words) - 22:24, 27 September 2024
  • Thumbnail for 1,3-dipole
    reactants in 1,3-dipolar cycloadditions. The dipole has at least one resonance structure with positive and negative charges having a 1,3 relationship...
    3 KB (228 words) - 16:45, 1 November 2023
  • reaction of münchnones and alkynes. The reaction mechanism involves 1,3-dipolar cycloaddition followed by loss of carbon dioxide by a retro-Diels–Alder process...
    34 KB (3,197 words) - 22:33, 22 May 2025
  • phosphorus) but 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...
    10 KB (1,151 words) - 16:23, 23 June 2025
  • following (3+2) cycloaddition protocols. A common technique for unsubstituted triazoles is the Huisgen azide-alkyne 1,3-dipolar cycloaddition: a azide and...
    10 KB (1,024 words) - 23:01, 1 May 2025
  • in 1,3-dipolar cycloadditions. Also 1,4-dipolars, 1,5-dipolars, and so on exist. Phosphonium ylide Diazomethane Carbonyl oxide Zwitterion Ylide 1,3-dipole...
    3 KB (324 words) - 10:05, 14 May 2025
  • Thumbnail for Isoindoline
    Isoindolines via One-Pot Sequential Cu(I)-Catalyzed Asymmetric 1,3-Dipolar Cycloaddition/Aromatization DOI: 10.1021/ol302987h Asymmetric organocatalytic...
    3 KB (275 words) - 16:19, 5 August 2024
  • Thumbnail for Orthogonality
    that fulfill the requirements of bioorthogonality, including the 1,3-dipolar cycloaddition between azides and cyclooctynes (also termed copper-free click...
    16 KB (2,698 words) - 18:06, 20 May 2025
  • Thumbnail for Phenyl isocyanate
    with triethylamine to activate nitro groups to undergo (C,O) 1,3-dipolar cycloaddition (as opposed to O,O). The nitro group (RCH2NO2) is converted to...
    4 KB (252 words) - 15:05, 24 March 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
  • Thumbnail for Nitrone
    application is intermediates in chemical synthesis. A nitrone is a 1,3-dipole used in cycloadditions, and a carbonyl mimic. Nitrones, as a tetrasubstituted double...
    6 KB (493 words) - 15:06, 21 May 2025
  • the Curtius rearrangement. Rolf Huisgen described the eponymous 1,3-dipolar cycloaddition. The interest in azides among organic chemists has been relatively...
    28 KB (2,857 words) - 10:40, 18 July 2025
  • Thumbnail for Tris(benzyltriazolylmethyl)amine
    copper(I), it allows for quantitative, regioselective formal Huisgen 1,3-dipolar cycloadditions between alkynes and azides, in a variety of aqueous and organic...
    4 KB (279 words) - 02:00, 22 August 2022
  • Thumbnail for Woodward–Hoffmann rules
    (4+2)-cycloaddition) is [π4s + π2s]. The 1,3-dipolar cycloaddition of ozone and an olefin in the first step of ozonolysis (a (3+2)-cycloaddition) is [π4s...
    88 KB (11,083 words) - 22:40, 30 June 2025
  • Ozonolysis (category Cycloadditions)
    or ketone (3) in a retro-1,3-dipolar cycloaddition. The oxide and aldehyde or ketone react again in a 1,3-dipolar cycloaddition, producing a relatively...
    16 KB (1,753 words) - 20:07, 25 June 2025
  • azides using phosphines: Diazo compounds react as 1,3-dipoles in diazoalkane 1,3-dipolar cycloadditions. Diazo compounds are used as precursors to carbenes...
    14 KB (1,511 words) - 20:44, 21 July 2025
  • agricultural insecticides. 2-Isoxazolines are generally produced by the 1,3-dipolar cycloaddition of nitrile oxides with alkenes. This has been applied in a diastereoselective...
    9 KB (732 words) - 22:56, 27 June 2025
  • Thumbnail for Aziridines
    These ylides can be trapped with a suitable dipolarophile in a 1,3-dipolar cycloaddition. When the N-substituent is an electron-withdrawing group such...
    16 KB (1,705 words) - 00:26, 17 July 2025
  • Thumbnail for Thioketone
    R2C=S=S, they are more usefully classified as 1,3-dipoles and indeed participate in 1,3-dipolar cycloadditions. Thiosulfines are proposed to exist in equilibrium...
    8 KB (941 words) - 23:56, 18 July 2025
  • or diazo compounds to generate the Diels–Alder or diazoalkane 1,3-dipolar cycloaddition products, respectively. Stable small-ring cycloalkynes have subsequently...
    14 KB (1,551 words) - 16:46, 5 July 2025
  • Examples include via a 1,3-dipolar cycloaddition of nitrile oxides with alkynes; or the reaction of hydroxylamine with 1,3-diketones or derivatives...
    7 KB (597 words) - 03:00, 14 May 2025
  • compounds or carbenes. N-heterocycles can be synthesized through 1,3-dipolar cycloaddition reactions. Ketone hydrazones are defunctionalized using mild reagents...
    4 KB (325 words) - 21:38, 25 November 2024
  • : 934–936  or halooxime elimination in base. They are used in 1,3-dipolar cycloadditions,: 1187–1192  such as to isoxazoles.: 1201–1202  They undergo type...
    32 KB (3,679 words) - 22:48, 6 July 2025