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Chemical reaction which forms a cyclic molecule
[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 more
Cycloaddition
Dipolar compound
consisting of an iminium ion next to a carbanion. They are used in 1,3-dipolar cycloaddition reactions to form five-membered heterocycles, including pyrrolidines
Azomethine_ylide
Modular approach to chemical synthesis
bonds. Not mentioned in this landmark review was the Huisgen 1,3-dipolar cycloaddition, possibly because it was slow. The year after publication of Sharpless's
Click_chemistry
German chemist (1920–2020)
achievement was the development of the 1,3-dipolar cycloaddition reaction, also called the Huisgen cycloaddition. Huisgen was born in Gerolstein in Rhineland-Palatinate
Rolf_Huisgen
Set of rules pertaining to pericyclic reactions
(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
Woodward–Hoffmann_rules
Class of chemical reactions
fulfill the requirements of bioorthogonality, including the 1,3-dipolar cycloaddition between azides and cyclooctynes (also termed copper-free click chemistry)
Bioorthogonal_chemistry
Organic compound
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
Ylide
Chemical compound
it allows for quantitative, regioselective formal Huisgen 1,3-dipolar cycloadditions between alkynes and azides, in a variety of aqueous and organic
Tris(benzyltriazolylmethyl)amine
Tris(benzyltriazolylmethyl)amine
American chemist and Nobel Laureate (born 1941)
PMID 11433435. Evans, Richard A. (2007). "The Rise of Azide–Alkyne 1,3-Dipolar 'Click' Cycloaddition and its Application to Polymer Science and Surface Modification"
Karl_Barry_Sharpless
Chemical reaction
trimethylenemethane cycloaddition and 1,3-dipolar cycloaddition, the eponymous synthon replaces the diene. In (4+3) cycloaddition, an allyl cation replaces
Diels–Alder_reaction
Organic compounds containing the azide (N3) functional group
Curtius rearrangement. Rolf Huisgen described the eponymous 1,3-dipolar cycloaddition. The interest in azides among organic chemists has been relatively
Organic_azide
Chemical compound
reactive nitrilimines. These can in turn undergo a variety of 1,3-dipolar cycloaddition reactions. Triazoles, analogs with three nitrogen atoms Pentazole
Tetrazole
Chemical compound
give acetonitrile N-oxide. The latter 1,3-dipole undergoes 1,3-dipolar cycloaddition to alkenes giving 2-isoxazolines in a one-pot procedure. This reaction
Acetaldoxime
Chemical compound
'volatile', recyclable dipolar, aprotic solvent for conducting substitution and cycloaddition reactions". Sustainable Chemical Processes. 3 (13). doi:10.1186/s40508-015-0040-7
Sulfolene
Cyclic amide
of an alkene with iodine. Lactams form by copper-catalyzed 1,3-dipolar cycloaddition of alkynes and nitrones in the Kinugasa reaction Diels-Alder reaction
Lactam
Chemical compound
synthesised via a variety of methods. Examples include via a 1,3-dipolar cycloaddition of nitrile oxides with alkynes; or the reaction of hydroxylamine
Isoxazole
Chemical compound
azides to yield a mixture of four products, arising from initial 1,3-dipolar cycloaddition onto either of the two olefins, followed by a retro-Diels–Alder
Oxanorbornadiene
Overview of and topical guide to organic chemistry
Volhard-Erdmann cyclization 1,3-Dipolar cycloaddition Azide-alkyne Huisgen cycloaddition Diels–Alder reaction Nitrone-olefin (3+2) cycloaddition Staudinger ketene-imine
Outline_of_organic_chemistry
Various meanings of the terms
fulfill the requirements of bioorthogonality, including the 1,3-dipolar cycloaddition between azides and cyclooctynes (also termed copper-free click chemistry)
Orthogonality
Chemical compound
"Alkaloid synthesis via the intramolecular imidate methylide 1,3-dipolar cycloaddition reaction". Tetrahedron. 41 (17): 3559–3568. doi:10.1016/S0040-4020(01)96709-2
Eserethole
Chemical compound
respiratory disease that respond to this type of treatment. The 1,3-dipolar cycloaddition between bromonitrile oxide, produced in situ from dibromoformaldoxime
Broxaterol
Hydrocarbon ring molecule containing a C≡C bond
diazo compounds to generate the Diels–Alder or diazoalkane 1,3-dipolar cycloaddition products, respectively. Stable small-ring cycloalkynes have subsequently
Cycloalkyne
Scottish organic chemist (born 1968)
asymmetric syntheses. Examples include Diels-Alder reactions, 1,3-dipolar cycloadditions, Friedel-Crafts alkylations or Michael additions. MacMillan has
David_MacMillan
Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides". Journal of Organic Chemistry. 67
Stapled_peptide
Chemical group (>C=N=N)
phosphines: Diazo compounds react as 1,3-dipoles in diazoalkane 1,3-dipolar cycloadditions. Diazo compounds are used as precursors to carbenes, which are generated
Diazo
Chemical compound
evaluated. R. A. Evans (2007). "The Rise of Azide–Alkyne 1,3-Dipolar 'Click' Cycloaddition and its Application to Polymer Science and Surface Modification"
3-Azidocoumarin
Area of research analysing the modification of carbon nanotubes
protocols for cycloadditions such as Diels-Alder reactions, 1,3-dipolar cycloadditions of azomethine ylides and azide–alkyne cycloaddition reactions. One
Carbon_nanotube_chemistry
Chemical compound
oxidation via Swern oxidation and oxime formation Intramolecular dipolar cycloaddition Selective control of diastereoisomer formation Removal of protection
Shishijimicin_A
Chemical compound
complex to ferrocene. HfCl4 increases the rate and control of 1,3-dipolar cycloadditions. It was found to yield better results than other Lewis acids when
Hafnium_tetrachloride
Chemical compound
cycloheptanone. This difference is consistent with stabilization of the dipolar resonance structure. Numerous methods exist for the organic synthesis of
Tropone
Synthesis of alkenes by base-catalysed decomposition of tosylhydrazones
either decompose to give the diazo compound and undergo a [3+2] dipolar cycloaddition with the aryne to give the product, or a [3+2] annulation with aryne
Bamford–Stevens_reaction
Chemical compound
Thujaplicins can be synthesized by cycloaddition of isopropylcyclopentadiene and dichloroketene, 1,3-dipolar cycloaddition of 5-isopropyl-1-methyl-3-oxidopyridinium
Thujaplicin
Antibiotic
and death. The key reaction in building the ring consists of 1,3-Dipolar cycloaddition of ethyl diazoacetate to N-Cbz-3-pyrroline to afford the pyrrazolidine
Trovafloxacin
Chemical compound
cofactor supports α,β-unsaturated acid decarboxylation via 1,3-dipolar cycloaddition". Nature. 522 (7557): 497–501. Bibcode:2015Natur.522..497P. doi:10
Prenylated flavin mononucleotide
Prenylated_flavin_mononucleotide
Naturally occurring sedative and hallucinogen
M, Sala A (1986). "A convenient synthesis of muscimol by a 1,3-dipolar cycloaddition reaction". Tetrahedron Letters. 27 (27): 3181–3182. doi:10
Muscimol
Organic ring compound (C4H4NH)
of münchnones and alkynes. The reaction mechanism involves 1,3-dipolar cycloaddition followed by loss of carbon dioxide by a retro-Diels–Alder process
Pyrrole
Chemical compound
to form an intermediate azomethine ylide, which underwent a 1,3-dipolar cycloaddition with an unsaturated oxindole also present in the reaction mixture
Spirotryprostatin_B
Cholesterol-lowering medication
pyrrole ring with Paal-Knorr cyclocondensation replaced the dipolar [3 + 2] cycloaddition from the earlier routes. The atorvastatin calcium complex involves
Atorvastatin
Chemical compound
thujaplicins, can be synthesized by cycloaddition of isopropylcyclopentadiene and dichloro ketene, 1,3-dipolar cycloaddition of 5-isopropyl-1-methyl-3-oxidopyridinium
Hinokitiol
Process that leads to chemical changes
molecule. An important example of cycloaddition reaction is the Diels–Alder reaction (the so-called [4+2] cycloaddition) between a conjugated diene and
Chemical_reaction
American chemist (born 1928)
doi:10.1021/jo970907o. Nair; et al. (2007). "Intramolecular 1,3-dipolar cycloaddition reactions in targeted syntheses". Tetrahedron. 63 (50): 12247–12275
Elias_James_Corey
Toxic plant alkaloid
synthesis of nominine via oxidoisoquinolinium-1,3-dipolar and dienamine-Diels-Alder cycloadditions". Journal of the American Chemical Society. 128 (27):
Aconitine
collaborated with M. Prato and others to outline a method using 1,3-dipolar cycloaddition to functionalize carbon nanotubes, yielding soluble bundles with
Dirk_M._Guldi
Discontinued SSRI antidepressant drug
"Synthesis and hSERT activity of homotryptamine analogs. Part 6: [3+2] dipolar cycloaddition of 3-vinylindoles". Bioorganic & Medicinal Chemistry Letters. 20
Indalpine
Chemical compound
Illudins and Ptaquilosin. A highly convergent approach via the dipolar cycloaddition of carbonyl ylides". Journal of the American Chemical Society. 116
Ptaquiloside
Analytical technique to study proteins
latent handle like an alkyne or azide for use with Huisgen 1,3-dipolar cycloaddition (also known as click chemistry). Reporter tags facilitate detection
Activity-based_proteomics
Chemical reaction
stereochemically defined allyl amine 3. Afterwards, the sequence of dipolar cycloaddition, base-mediated N–O bond breakage and hydrolysis then complete the
Petasis_reaction
German and Italian physicist
"Adhesion of Photon-Driven Molecular Motors to Surfaces via 1,3-Dipolar Cycloadditions: Effect of Interfacial Interactions on Molecular Motion" (PDF).
Petra_Rudolf
Russian organic and medicinal chemist. (1935–2017)
interests of N.S. Zefirov. It can react as a good dipole in 1,3-dipolar cycloaddition with alkenes. It was found, that the reaction of C(NO2)4 with a
Nikolay_Zefirov
Emerging technology field
"Adhesion of Photon-Driven Molecular Motors to Surfacesvia1,3-Dipolar Cycloadditions: Effect of Interfacial Interactions on Molecular Motion" (PDF).
Nanorobotics
Simplest diazo compound and methylating agent
used as a carbene source. It readily takes part in diazoalkane 1,3-dipolar cycloadditions. A wide variety of routes have been developed for the laboratory
Diazomethane
Use of metal-based Lewis acids to catalyze organic reactions
Lewis acid and the identity of the R' group. In Diels-Alder and 1,3-dipolar cycloaddition reactions, Lewis acids lower the LUMO energy of the dienophile or
Lewis_acid_catalysis
Chemistry of carbon's allotrope fullerene
[2+2]cycloadditions for instance with benzyne. An example of a 1,3-dipolar cycloaddition to a 5-membered ring is the Prato reaction. Fullerenes are easily
Fullerene_chemistry
3-dipolar cycloaddition of a cyclooctynes and an azide was carried out forming a covalent linkage (also termed the Cu-free azide-alkyne cycloaddition)
Aldehyde_tag
Dutch Nobel laureate in chemistry
"Adhesion of Photon-Driven Molecular Motors to Surfaces via 1,3-Dipolar Cycloadditions: Effect of Interfacial Interactions on Molecular Motion" (PDF).
Ben_Feringa
Scientific theory
structures for 1,3-dipoles and for the diradical intermediates in 1,3-dipolar cycloadditions". Journal of the Chemical Society A: Inorganic, Physical, Theoretical:
Linnett_double-quartet_theory
Orchestra), COVID-19. Rolf Huisgen, 99, German chemist, developer of 1,3-Dipolar cycloaddition. John Hyde, 89, Australian footballer (Geelong), cancer. Oscar Ichazo
Deaths_in_March_2020
Organic compound with a –C≡N functional group
halooxime elimination in base. They are highly reactive in 1,3-dipolar cycloadditions, such as to isoxazoles, and undergo type I dyotropic rearrangement
Nitrile
13 DIPOLAR-CYCLOADDITION
13 DIPOLAR-CYCLOADDITION
13 DIPOLAR-CYCLOADDITION
13 DIPOLAR-CYCLOADDITION
13 DIPOLAR-CYCLOADDITION
13 DIPOLAR-CYCLOADDITION
13 DIPOLAR-CYCLOADDITION
13 DIPOLAR-CYCLOADDITION
13 DIPOLAR-CYCLOADDITION