Cycloaddition Reaction
Cyclization
Alkynes
Click Chemistry
Organic chemistry methodology that mimics the modular nature of various biosynthetic processes. It uses highly reliable and selective reactions designed to "click" i.e., rapidly join small modular units together in high yield, without offensive byproducts. In combination with COMBINATORIAL CHEMISTRY TECHNIQUES, it is used for the synthesis of new compounds and combinatorial libraries.
Rhodium
Stereoisomerism
Alkenes
Molecular Structure
Sinomenium
Organogold Compounds
Catalysis
Sesquiterpenes, Guaiane
Spiro Compounds
Combinatorial Chemistry Techniques
Carbonic Acid
Indolizidines
Copper
Hydrocarbons, Cyclic
Cycloparaffins
Alicyclic hydrocarbons in which three or more of the carbon atoms in each molecule are united in a ring structure and each of the ring carbon atoms is joined to two hydrogen atoms or alkyl groups. The simplest members are cyclopropane (C3H6), cyclobutane (C4H8), cyclohexane (C6H12), and derivatives of these such as methylcyclohexane (C6H11CH3). (From Sax, et al., Hawley's Condensed Chemical Dictionary, 11th ed)
Indicators and Reagents
Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)
Palladium
Models, Molecular
Magnetic Resonance Spectroscopy
Sydnones
Heterocyclic Compounds
Furans
Vincamine
Total synthesis of (+)-nankakurines A and B and (+/-)-5-epi-nankakurine A. (1/73)
(+info)Tyrosine-lipid peroxide adducts from radical termination: para coupling and intramolecular Diels-Alder cyclization. (2/73)
(+info)Interception of a Rautenstrauch intermediate by alkynes for [5+2] cycloaddition: rhodium-catalyzed cycloisomerization of 3-acyloxy-4-ene-1,9-diynes to bicyclo[5.3.0]decatrienes. (3/73)
(+info)Increasing the efficacy of bioorthogonal click reactions for bioconjugation: a comparative study. (4/73)
(+info)The chemical synthesis of tetrodoxin: an ongoing quest. (5/73)
(+info)Detection of transglutaminase activity using click chemistry. (6/73)
(+info)Total synthesis of (+/-)-sorocenol B employing nanoparticle catalysis. (7/73)
(+info)Effects of trehalose polycation end-group functionalization on plasmid DNA uptake and transfection. (8/73)
(+info)
Tetrazine ligation for chemical proteomics | Proteome Science | Full Text
Tetrazine ligation for chemical proteomics | Proteome Science | Full Text
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Metal-centered cycloaddition reactions
A metal-centered cycloaddition is a subtype of the more general class of cycloaddition reactions. In such reactions "two or ... Cycloaddition reaction Frontier Molecular Orbital Theory Organometallic chemistry Pericyclic reaction 1,3-Dipolar cycloaddition ... Alkylidenes and other carbene analogs participate readily in cycloaddition reactions. Cycloaddition reactions of Ruthenium ... thereby catalyzing the reaction the Diels-Alder reaction. A crucial role of the metal in many cycloadditions reactions is to ...
Bradsher cycloaddition
The Bradsher cycloaddition reaction, also known as the Bradsher cyclization reaction is a form of the Diels-Alder reaction ... The Bradsher cycloaddition was first reported by C. K. Bradsher and T. W. G. Solomons in 1958. C. K. Bradsher, T. W. G. ... II.1The Diels-Alder Reaction". J. Am. Chem. Soc. 80 (4): 933. doi:10.1021/ja01537a045. Merck Index, 14th Ed. C. K. Bradsher, J ...
Trimethylenemethane cycloaddition
... cycloaddition reactions involving this class of reaction intermediates. The problem is generally less severe for five-membered ... The high stereospecificity and stereoselectivity inherent in many TMM cycloaddition reactions is a significant advantage; for ... Reactions of diazenes should employ degassed solvents to avoid radical reactions with oxygen. Tetrahydrofuran (THF) at reflux ... reagents which can generate TMM or TMM synthons in situ can be used to effect cycloaddition reactions with appropriate electron ...
Intramolecular Diels-Alder cycloaddition
The reaction leads to the formation of the same cyclohexene-like structure as usual for a Diels-Alder reaction, but as part of ... In organic chemistry, an intramolecular Diels-Alder cycloaddition is a Diels-Alder reaction in which the diene and a dienophile ... Diels-Alder reaction effects. Intramolecular Diels-Alder cycloaddition is extremely useful for the formation of naturally ... This reaction gives rise to various natural derivatives of decalin. Because the two reacting groups are already attached, two ...
Diazoalkane 1,3-dipolar cycloaddition
The reaction product of a cycloaddition between diazomethane and trans-diethyl glutaconate is a 1-pyrazoline. This reaction is ... The Diazoalkane 1,3-dipolar cycloaddition is a 1,3-dipolar cycloaddition (an organic reaction) between a 1,3-dipole diazo ... The reaction is also a syn addition, and the configuration in the dipolarophile is preserved. The 1-pyrazoline is unstable and ... With diazo(phenyl)methane as the reactant the regioselectivity is reversed and the reaction is extended even further by simple ...
Rolf Huisgen
3-dipolar cycloaddition reaction, also known as the Huisgen cycloaddition or Huisgen reaction. The Huisgen reaction is of ... His major achievement was the development of the 1,3-dipolar cycloaddition reaction, also called the Huisgen cycloaddition. ... "Cycloaddition reactions of alkenes". The Alkenes: Vol. 1 (1964). Chichester, UK: John Wiley & Sons, Ltd. pp. 739-953. doi: ... Huisgen, Rolf (1994). The adventure playground of mechanisms and novel reactions. Washington, DC: American Chemical Society. ...
Topochemical polymerization
Hema, Kuntrapakam; Sureshan, Kana M. (2019-11-19). "Topochemical Azide-Alkyne Cycloaddition Reaction". Accounts of Chemical ... Hema, Kuntrapakam; Sureshan, Kana M. (2019-11-19). "Topochemical Azide-Alkyne Cycloaddition Reaction". Accounts of Chemical ... permutative azide-alkyne cycloaddition reactions leading to a vast library of products in the crystal". CrystEngComm. 20 (11): ... cycloaddition reaction involving coordination polymers". Chemical Communications. 52 (21): 3989-4001. doi:10.1039/c5cc08374e. ...
Prato reaction
The Prato reaction is a particular example of the well-known 1,3-dipolar cycloaddition of azomethine ylides to olefins. In ... Just as in other fullerene reactions like the Bingel reaction or Diels-Alder reactions this reaction can be reversed. A thermal ... Martín N, Altable M, Filippone S, Martín-Domenech A, Echegoyen L, Cardona CM (2006). "Retro-Cycloaddition Reaction of ... It is known that the Prato reaction is very useful to functionalize endohedral metallofullerenes. Prato reaction on [email protected] ...
Benzylamine
Cycloaddition Reactions in Organic Synthesis. John Wiley & Sons. pp. 187-210. ISBN 9783527301591. Grieco, P. A.; Larsen, S. D ... an exemplar of the Schotten-Baumann reaction first described in the 1880s. The reaction takes place in a two-phase solvent ... It was first produced accidentally by Rudolf Leuckart in the reaction of benzaldehyde with formamide in a process now known as ... The aza-Diels-Alder reaction converts imines and dienes to tetrahydropyridines in which the nitrogen atom can be part of the ...
Organosulfur compounds
Photogeneration, rearrangement, and cycloaddition reactions". J. Am. Chem. Soc. 98 (12): 3564-3572. doi:10.1021/ja00428a029. ... In one named reaction called the Ferrario reaction phenyl ether is converted to phenoxathiin by action of elemental sulfur and ... was discovered in 1990 by reaction of tetramethyltellurium with xenon difluoride to TeF2(CH3)4 followed by reaction with ... Certain aromatic thiols can be accessed through a Herz reaction. Disulfides R−S−S−R with a covalent sulfur to sulfur bond are ...
Phosphole
... s undergo different cycloaddition reactions; coordination properties of phospholes are also well studied. The parent ... One route to phospholes is via the McCormack reaction, involving the addition of a 1,3-diene to a phosphonous chloride (RPCl2) ... For example, they undergo Diels-Alder reactions with electrophilic alkynes. They are basic at P, serving as ligands. 2,5- ... Phenylphospholes can be prepared via zirconacyclopentadienes by reaction with PhPCl2. The behavior of the secondary phospholes ...
Thioketene
I. Synthesis and cycloaddition reactions". J. Org. Chem. 35 (10): 3470-3483. doi:10.1021/jo00835a064. Dekant, Wolfgang; Urban, ...
Cycloaddition
The Huisgen cycloaddition reaction is a (2+3)cycloaddition. The Nitrone-olefin cycloaddition is a (3+2)cycloaddition. ... In this notation, the DA reaction and the dipolar reaction both become a [4+2]cycloaddition. The reaction between norbornadiene ... The classic example is the reaction of sulfur dioxide with a diene. Other cycloaddition reactions exist: [4+3] cycloadditions ... 3-dipolar cycloaddition is also a [4 + 2]-cycloaddition. Thermal cycloadditions are those cycloadditions where the reactants ...
Norbornadiene
... is reactive in cycloaddition reactions. Norbornadiene is also the starting material for the synthesis of ... Norbornadiene is also a useful dienophile in Diels-Alder reactions. Norbornadiene can be formed by a Diels-Alder reaction ... in reactions with phosphine ligands. Norbornane a saturated compound with the same carbon skeleton. Norbornene a compound with ... The Role of 7-Substituents in Governing the Facial Selectivity for the Diels-Alder Reaction of Benzonorbornadienes with 3,6-Di( ...
Captodative effect
Stella, L. (1986). "Captodative Substituent Effects in Cycloaddition Reactions". In Viehe, H. G.; Janousek, Z.; Merényi, R. ( ... Thus, the reaction is slow relative to the R = OCH2CH3 case. When R = CH3, the rate of the reaction is faster relative to when ... Radical reactions play an integral role in several chemical reactions and are also important to the field of polymer science. ... When R = OCH2CH3, the rate of the reaction is the fastest because the reaction has the smallest energy of activation (ΔG‡). The ...
Chiral auxiliary
Evans, D. A.; Chapman, K. T.; Bisaha, J. (1984). "New Asymmetric Diels-Alder Cycloaddition Reactions. Chiral α,β-Unsaturated ... including aldol reactions, alkylation reactions, and Diels-Alder reactions. The oxazolidinones are substituted at the 4 and 5 ... utilizes oxazolidinone chiral auxiliaries for one asymmetric alkylation reaction and four asymmetric aldol reactions, setting ... The cycloaddition product was carried forward to the iodolactone shown below, an intermediate in the classic Corey synthesis of ...
Hexadehydro Diels-Alder reaction
This reaction is a derivative of the established Diels-Alder reaction and proceeds via a similar [4+2] cycloaddition mechanism ... The HDDA reaction can be used in a cascade reaction sequence with ene reactions, such as the Alder ene reaction and the ... including reaction solvents. Thus, in practice the HDDA reaction describes a two-step cascade reaction of benzyne formation and ... The simplest model of an HDDA reaction is the cycloaddition of butadiyne and acetylene to form ortho-benzyne (o-benzyne, shown ...
Conia-ene reaction
Having obtained silyl enol ether 7 in 11 steps from bicycle 6, itself the product of a Diels-Alder cycloaddition between ... As initially reported by J. M. Conia and P. Le Perchec, the Conia-ene reaction is a heteroatom analog of the ene reaction that ... Like other pericyclic reactions, the original Conia-ene reaction required high temperatures to proceed, limiting its wider ... In the decades after the discovery of the Conia-ene reaction, several improvements allowed for milder reaction conditions and ...
Imine Diels-Alder reaction
Cycloadditions of these intermediates with dienes give single constitutional isomers, but proceed with moderate ... The reaction may be thermal, in refluxing solvents such as benzene or others typical for Diels-Alder reactions, or acid ... 15) Oxo Diels-Alder reaction Aza-Diels-Alder reaction Heintzelman, G. R.; Meigh, I. R.; Mahajan, Y. R.; Weinreb, S. M. (2005 ... Imines may be employed as dienophiles in hetero-Diels-Alder reactions. These reactions involve the lowest unoccupied molecular ...
Enone-alkene cycloadditions
In organic chemistry, enone-alkene cycloadditions are a version of the [2+2] cycloaddition This reaction involves an enone and ... Enone-alkene cycloadditions often suffer from side reactions, e.g. those associated with the diradical intermediate. These side ... Intramolecular enone-alkene cycloaddition may give either "bent" or "straight" products depending on the reaction ... This energy-wasting process competes with cycloaddition and is evident in reactions that yield mixtures of cis- and trans-fused ...
Diels-Alder reaction
Bradsher cycloaddition Wagner-Jauregg reaction Imine Diels-Alder reaction Aza-Diels-Alder reaction Diels-Alderases, enzymes ... Cycloadditions, Name reactions, Carbon-carbon bond forming reactions, Ring forming reactions, German inventions, 1928 in ... this reverse reaction is known as the retro-Diels-Alder reaction. The reaction is an example of a concerted pericyclic reaction ... Diels-Alder reactions, as concerted cycloadditions, are stereospecific. Stereochemical information of the diene and the ...
Alkene carboamination
Coldham, I.; Hufton, R. (2005). "Intramolecular dipolar cycloaddition reactions of azomethine ylides". Chem. Rev. 105 (7): 2765 ... In this reaction, enoxyphthalimide was used to serve as both the nitrogen and carbon source. The reaction mechanism is proposed ... The reaction mechanism varies with different transition metals. For palladium-catalyzed carboamination reactions, Pd(0)/Pd(II) ... Generally, there are four categories of reaction modes for alkene carboamination. The first class is cyclization reactions, ...
Nitrone-olefin (3+2) cycloaddition
... cycloaddition process. This reaction is a 1,3-dipolar cycloaddition, in which the nitrone acts as the 1,3-dipole, and the ... The nitrone-olefin (3+2) cycloaddition reaction is the combination of a nitrone with an alkene or alkyne to generate an ... These reactions generally take place at much lower temperatures than intermolecular cycloadditions. Regiochemistry is more ... Alkynes can also serve as dipolarophiles in this reaction. The rules for predicting alkene cycloaddition products based on the ...
1,3-Dipolar cycloaddition
3-dipolar cycloaddition reaction. The stereoselectivity of 1,3-dipolar cycloaddition reactions between carbonyl ylide dipoles ... 1,3-dipolar cycloaddition with nitrile oxides is a widely used masked-aldol reaction. Cycloaddition between a nitrile oxide and ... Using competition reaction experiments, relative rates of addition for different cycloaddition reactions have been found to ... 3-dipolar cycloaddition reaction with methyl propiolate and methyl propargyl ether. The reaction with methyl propiolate affords ...
Late-stage functionalization
Jewett, John C.; Bertozzi, Carolyn R. (2010-03-22). "Cu-free click cycloaddition reactions in chemical biology". Chemical ... All LSF reactions are chemoselective but not every chemoselective reaction fulfills the requirements of the definition for LSF ... The requirements for LSF can be met by both C-H functionalization reactions and functional group manipulations. LSF reactions ... In contrast, bioorthogonal 1,3-dipolar cycloadditions (see also copper-free click chemistry and Huisgen cycloaddition) ...
Alkyne trimerisation
... cycloaddition reaction in which three alkyne units (C≡C) react to form a benzene ring. The reaction requires a metal catalyst. ... Carbon-carbon bond forming reactions, Cycloadditions, Multiple component reactions). ... Being a cycloaddition reaction, it has high atom economy. Many variations have been developed, including cyclisation of ... Wills, M. S. B.; Danheiser, R. L. (1998). "Intramolecular [4 + 2] Cycloaddition Reactions of Conjugated Ynones. Formation of ...
1,2-Dichloroethene
Both isomers participate in Kumada coupling reactions. trans-1,2-Dichloroethylene participates in cycloaddition reactions. ... "Arene synthesis by extrusion reaction. 16. Coplanar and stable derivatives of 13,14-didehydro-tribenzo[a,c,e]cyclooctene: ...
Ynone
Cycloaddition Reactions of Conjugated Ynones. Formation of Polycyclic Furans via the Generation and Rearrangement of Strained ... An alternative but longer synthetic method involves the reaction of an alkynyllithium compound with an aldehyde. The reaction ... The reaction affords γ,δ-ynones. Terminal alkynes add across epoxides to given yneols, which can be oxidized to give β,γ-ynones ... One method for synthesizing ynones is the acyl substitution reaction of an alkynyldimethylaluminum with an acyl chloride. An ...
Rick L. Danheiser
... cycloadditions based on propargylic ene reaction/Diels-Alder cycloaddition cascades. Natural products synthesized in his ... Cycloaddition Reactions of Conjugated Enynes". J. Org. Chem. 59 (19): 5514. doi:10.1021/jo00098a002. Sakai, T.; Danheiser, R. L ... 2010). "Cyano Diels-Alder and Cyano Ene Reactions. Applications in a Formal [2 + 2 +2] Cycloaddition Strategy for the Synthesis ... Application of Iminoacetonitrile Cycloadditions in Organic Synthesis". Org. Lett. 7 (14): 3115-3118. doi:10.1021/ol051185n. PMC ...
Alkyne
... s undergo diverse cycloaddition reactions. The Diels-Alder reaction with 1,3-dienes give 1,4-cyclohexadienes. This ... Other specialized cycloadditions include multicomponent reactions such as alkyne trimerisation to give aromatic compounds and ... This reaction was once a major industrial process but it has been displaced by the Wacker process. This reaction occurs in ... The hydration reaction of acetylene gives acetaldehyde. The reaction proceeds by formation of vinyl alcohol, which undergoes ...
Xylylene
"Lewis acid-promoted generation of α-oxy-o-quinodimethanes and cycloaddition reactions". Tetrahedron Letters. 35 (23): 3975-3978 ... For example, reaction of α,α'-dibromo-o-xylene with iron carbonyls affords low yields of the xylylene complex Fe(CO)3[η4-C6H4( ... For example, reaction of tetrabromo-o-xylene (C6H4(CHBr2)2) with sodium iodide affords α,α'-dibromo-o-xylylene, which can be ... This and other syntheses of o-xylylenes, and their subsequent dimerization by [4+4] cycloaddition to form cycloctyl structures ...
Münchnone
... s are typically used as 1,3-dipolar cycloaddition substrates in the synthesis of pyrroles by their in situ generation ... The azomethine ylide reactivity of münchnones, and their reaction with alkynes in the synthesis of pyrroles, was first ... doi:10.1002/9780470187289.ch4) Gribble, G. W. In Oxazoles: Synthesis, Reactions, and Spectroscopy, A; Palmer, D. C., Ed.; Wiley ...
1,2,4,5-Tetrabromobenzene
... cycloadditions with 1,2,4,5-tetrabromobenzene sometimes proceed in very high yields, such as the reaction of a dihalogen- ... This reaction can also be carried out in a laboratory experiment with excess bromine and iron nails (as starting material for ... The endoxide reacts with 3-sulfolene in a Diels-Alder reaction upon elimination of sulfur dioxide. The resulting tricyclic ... In a one-pot reaction, 1,2,4,5-tetrabromobenzene reacts with 4-hydroxybenzaldehyde, the alkylating agent 1-bromopentane, the ...
Stannole
1,1-Disubstituted stannoles can be formed in the [2+2+1] cycloaddition reaction of two acetylene molecules with an organotin ... 1,1-Dimethyl-2,3,4,5-tetraphenyl-1H-stannole, for example, can be formed by the reaction of 1,4-dilithio-1,2,3,4-tetraphenyl-1, ...
Intramolecular reaction
... cycloaddition reactions of tethered l-(+)-valinol derived tetrahydrophthalimides". Chem. Commun. 1997 (15): 1385-1386. doi: ... an SN2 reaction within the same molecule) In intramolecular organic reactions, two reaction sites are contained within a single ... many intramolecular reactions that would not occur as an intermolecular reaction between two compounds take place. Examples of ... otherwise-intermolecular reactions can be made temporarily intramolecular by anchoring both reactions by a tether with all the ...
Ene reaction
Just as in the case of any cycloaddition, the success of an ene reaction is largely determined by the steric accessibility of ... Similarly, ene reactions with enols or enolates are classified as Conia-ene and Conia-ene-type reactions. In addition, ene ... Thermal ene reactions have several drawbacks, such as the need for very high temperatures and the possibility of side reactions ... Diels-Alder reaction Thiol-ene reaction Certain isotoluenes isomerize by an ene mechanism Alder, K.; Pascher, F; Schmitz, A. " ...
1-Phosphaallenes
The reaction of phosphaallenes with dichlorocarbenes results in a [2+1]-cycloaddition to the P=C double bond, which results in ... As many of these reactions are warmed, oligomerization of the phosphaallene occurs. Other reactions following this synthetic ... Cycloaddition Reactions between Group 14 Heteroallenes and Triple Bonds". The Journal of Organic Chemistry. 76 (7): 2310-2314. ... Many of these reactions require temperatures between -90°C and 0°C to ensure a stable product is formed. ...
Aziridines
"Hoch-Campbell Reaction". Comprehensive Organic Name Reactions and Reagents. 2010. doi:10.1002/9780470638859.conrr320. ISBN ... These ylides can be trapped with a suitable dipolarophile in a 1,3-dipolar cycloaddition. When the N-substituent is an electron ... followed by ring closing with the Mitsunobu reaction. The Hoch-Campbell ethylenimine synthesis involves the reaction of certain ... One method involves the ring-opening reaction of an epoxide with sodium azide, followed by reduction of the azide with ...
Hans-Ulrich Reissig
His research interests include the development of new synthetic methods, the investigation of reaction mechanisms and the ... the use of samarium diiodide in synthesis and cycloadditions of nitroso alkenes. Besides the synthesis of a broad range of ... He is particularly interested in reactions of lithiated alkoxyallenes, ... Nonafluorobutanesulfonates as Intermediates for Transition Metal-Catalyzed Reactions". Advanced Synthesis & Catalysis. 351 (17 ...
Intrinsic bond orbitals
... cycloaddition of a phosphaalkene to an arene has likewise led to insightful results regarding the specifics of the reaction ... The value of IBO analysis along the IRC especially shows for complex reactions, such as a cyclopropanation reaction with only ... The previously thought single step C-H activation reaction was in this case revealed to consist of three distinct phases: i) ... In 2015, Knizia and Klein introduced the analysis of electron flow in reactions with IBO as a non-empirical and straight- ...
Chiral Lewis acid
Common reaction types include Diels-Alder reactions, the ene reaction, [2+2] cycloaddition reactions, hydrocyanation of ... catalyzes a number of diene-aldehyde cycloaddition reactions. In the aldol reaction, the diastereoselectivity of the product is ... Diels-Alder reactions occur between a conjugated diene and an alkene (commonly known as the dienophile). This cycloaddition ... Reactions catalyzed by tin-based CLAs allow products to deviate from this pattern. The transition structures for reactions with ...
Petasis reaction
Wong and coworkers prepared N-acetylneuraminic acid with a PBM coupling, followed by nitrone-[3+2] cycloaddition. Vinylboronic ... Coupling reactions, Multiple component reactions, Substitution reactions, Name reactions, Chemical synthesis of amino acids). ... The Petasis reaction (alternatively called the Petasis borono-Mannich (PBM) reaction) is the multi-component reaction of an ... Additionally, the reaction does not require anhydrous or inert conditions. As a mild, selective synthesis, the Petasis reaction ...
Bioorthogonal chemistry
This isocyanide click reaction is a [4+1] cycloaddition followed by a retro-Diels Alder elimination of N2. The reaction ... The oxanorbornadiene cycloaddition is a 1,3-dipolar cycloaddition followed by a retro-Diels Alder reaction to generate a ... 1,3 dipolar cycloadditions have been developed as a bioorthogonal reaction using a nitrile oxide as a 1,3-dipole and a ... This cycloaddition between a nitrone and a cyclooctyne forms N-alkylated isoxazolines. The reaction rate is enhanced by water ...
Staudinger synthesis
2 cycloaddition to produce a β-lactam 3. The reaction carries particular importance in the synthesis of β-lactam antibiotics. ... The reaction was discovered in 1907 by the German chemist Hermann Staudinger. The reaction did not attract interest until the ... The reaction occurs by a rhodium acetate-catalyzed reaction between the aryldiazoacetate (red) and the organic azide (blue) to ... The yield of the reaction is about 99%. The reaction with sulfenes instead of ketenes leading to β-sultams is called Sulfa- ...
2.2.2-Propellane
... followed by elimination reaction with potassium t-butoxide of acetic acid to cyclobutene 3, followed by another cycloaddition ... and reaction with tosyl azide. The ketone then undergoes Wolff rearrangement to ketene 6. Ozonolysis forms the ketone 7, ... cycloaddition of ethylene on the cyclohexene derivative 1 to produce the bicyclic compound 2, ... another diazotation yields the diazo ketone 8, which undergoes Wolff rearrangement again to the ketene 9. Reaction with ...
Aflatoxin total synthesis
This reaction is catalyzed by a CBS catalyst and is enantioselective. The next step is the orthoformylation of reaction product ... The total synthesis of Aflatoxin B2 is a multistep sequence that begins with a [2+3]cycloaddition between the quinone 1 and the ... In the final step the coumarin skeleton is added to 9 by a combined coupling reaction with zinc carbonate of the vinyl bromide ... This step enables a Grignard reaction of the aldehyde group in 4 with methylmagnesiumbromide to the alcohol 5 which is then ...
Tricyclobutabenzene
Soc.; 2006; 128(11) pp 3534 - 3535; doi:10.1021/ja0602647 Reaction sequence: the key step is a [2+2] cycloaddition between an ... doi:10.1021/ja00497a064 Reaction sequence: coupling reaction of cyclobutene Grignard reagents followed by Diels-Alder reaction ... The silyl acetal is then converted to a ketone group by hydrofluoric acid and the remaining acetal groups by reaction with ... Cycloaddition of Benzyne and Ketene Silyl Acetal Toshiyuki Hamura, Yousuke Ibusuki, Hidehiro Uekusa, Takashi Matsumoto, and ...
Povarov reaction
Cycloadditions, Multiple component reactions, Quinoline forming reactions, Name reactions). ... The Povarov reaction is an organic reaction described as a formal cycloaddition between an aromatic imine and an alkene. The ... The reaction product in the original Povarov reaction is a quinoline. Because the reactions can be carried out with the three ... The reaction is also classified as a subset of aza Diels-Alder reactions The reaction depicted in Scheme 2 illustrates the ...
Vinylcyclopropane (5+2) cycloaddition
Since the initial report of a rhodium-catalyzed VCP [5+2] cycloaddition from Paul A. Wender's research group, other reaction ... Ylijoki KE, Stryker JM (March 2013). "[5 + 2] cycloaddition reactions in organic and natural product synthesis". Chemical ... Vinylcyclopropane [5+2] cycloaddition is a type of cycloaddition between a vinylcyclopropane (VCP) and an olefin or alkyne to ... The proposed reaction mechanism involves an initial [2+2] cycloaddition between the vinylcyclopropane and TCNE, followed by ...
Tetramethylurea
Tetrakis(dimethylamino)ethylene (TDAE) reacts with oxygen in a (2+2) cycloaddition reaction to a 1,2-dioxetane which decomposes ... The reaction of dimethylamine with phosgene in the presence of e. g. 50 % sodium hydroxide solution and subsequent extraction ... The reactions with dimethylcarbamoyl chloride or phosgene are highly exothermic and the removal of the resulting dimethylamine ... The reaction of diphenylcarbonate with dimethylamine in an autoclave is also effective. Tetramethylurea is formed in the ...
Tert-Butylphosphaacetylene
... cycloadditions. tert-Butylphosphaacetylene also undergoes a homo Diels-Alder cycloaddition reaction. Becker, Gerd; Gresser, ... The synthesis of t-BuCP entails the reaction of pivaloyl chloride and P(SiMe3)3. The reaction proceeds via the intermediacy of ... Carrying out the phosphoalkene reaction at 120-200 °C in the presence of catalytic amounts of solid NaOH forms the final t-BuCP ... doi:10.1016/S0040-4039(00)83969-6. Arif, Atta M.; Barron, Andrew R.; Cowley, Alan H.; Hall, Stephen W. "Reaction of the phospha ...
Anthracene
... also reacts with dienophile singlet oxygen in a [4+2]-cycloaddition (Diels-Alder reaction): Chemical oxidation ... Rickborn, Bruce (1998). "The Retro-Diels-Alder Reaction Part I. C−C Dienophiles". Organic Reactions. pp. 1-393. doi:10.1002/ ... The reaction is affected by the presence of oxygen. ... cycloaddition. It reverts to anthracene thermally or with UV ... or o-methylene-substituted diarylketones in the so-called Elbs reaction, for example from o-tolyl phenyl ketone. Reduction of ...
Selone
It is known to undergo cycloaddition with 1,3-dienes in a reaction similar to the Diels-Alder reaction. J. Peng; J. D. Odom; R ... Chiral oxazolidineselones can be used for stereoselective control of aldol reactions, analogous to the Evans aldol reaction ... Erker, G.; Hock, R.; Krüger, C.; Werner, S.; Klärner, F. G.; Artschwager-Perl, U. (1990). "Synthesis and Cycloadditions of ... 2009). "Chiral N-Acetyl Selone-Promoted Aldol Reactions". Synthetic Communications. 39 (4): 641-653. doi:10.1080/ ...
Petra Rudolf
3-Dipolar Cycloadditions: Effect of Interfacial Interactions on Molecular Motion" (PDF). ACS Nano. 5 (1): 622-630. doi:10.1021/ ... "Laccase-Functionalized Graphene Oxide Assemblies as Efficient Nanobiocatalysts for Oxidation Reactions". Sensors. 16 (3): 287. ...
Nitroalkene
... s are synthesized by various means, notable examples include: Nitroaldol reactions such as the Henry reaction: ... Nitroalkene acting as an activated dienophile toward butadiene in a Diels-Alder cycloaddition: The synthesis of pyrrole ... making the functional group useful in specialty reactions such as the Michael reaction or Diels-Alder additions. ... DiRocco, D. A.; Oberg, K. M.; Dalton, D. M.; Rovis, T. (2009). "Catalytic Asymmetric Intermolecular Stetter Reaction of ...
Computational calculations in microwave-assisted organic synthesis (MAOS). Application to cycloaddition reactions - Université...
Studies Directed at the Synthesis of Optically Active Pretazettine via Intramolecular Nitrone/Alkene Cycloaddition Reactions |...
Studies Directed at the Synthesis of Optically Active Pretazettine via Intramolecular Nitrone/Alkene Cycloaddition Reactions ... Studies Directed at the Synthesis of Optically Active Pretazettine via Intramolecular Nitrone/Alkene Cycloaddition Reactions ... 3-dipolar cycloaddition to afford the two diastereomeric isoxazolidine cycloadducts in a 16:1 ratio. The sense of chirality ...
Combining two-directional synthesis and tandem reactions: desymmetrisation by intramolecular cycloaddition/triazoline...
title = "Combining two-directional synthesis and tandem reactions: desymmetrisation by intramolecular cycloaddition/triazoline ... T1 - Combining two-directional synthesis and tandem reactions: desymmetrisation by intramolecular cycloaddition/triazoline ... Combining two-directional synthesis and tandem reactions: desymmetrisation by intramolecular cycloaddition/triazoline ... Combining two-directional synthesis and tandem reactions: desymmetrisation by intramolecular cycloaddition/triazoline ...
A novel synthesis of the 1β-methylcarbapenem key intermediate employing the [2+2]-cycloaddition reaction of chlorosulfonyl...
A highly stereoselective synthetic route to the title compound was explored by featuring the [2+2]-cycloaddition reaction of ... N2 - A highly stereoselective synthetic route to the title compound was explored by featuring the [2+2]-cycloaddition reaction ... AB - A highly stereoselective synthetic route to the title compound was explored by featuring the [2+2]-cycloaddition reaction ... T1 - A novel synthesis of the 1β-methylcarbapenem key intermediate employing the [2+2]-cycloaddition reaction of chlorosulfonyl ...
Nickel-catalyzed [2 + 2 + 2] cycloaddition reaction of isocyanates with 1,3-dienes<...
Morimoto M, Nishida Y, Miura T, Murakami M. Nickel-catalyzed [2 + 2 + 2] cycloaddition reaction of isocyanates with 1,3-dienes ... Morimoto, M, Nishida, Y, Miura, T & Murakami, M 2013, Nickel-catalyzed [2 + 2 + 2] cycloaddition reaction of isocyanates with ... Nickel-catalyzed [2 + 2 + 2] cycloaddition reaction of isocyanates with 1,3-dienes. In: Chemistry Letters. 2013 ; Vol. 42, No. ... Morimoto, M., Nishida, Y., Miura, T., & Murakami, M. (2013). Nickel-catalyzed [2 + 2 + 2] cycloaddition reaction of isocyanates ...
Theoretical Study on the Mechanism of the Cycloaddition Reactions Between Methyleneketene and 5-methylene-1,3-dioxan-4,6-dione
Three different reaction schemes for the cycloaddition reactions between methyleneketene and 5-methylene-1,3-dioxan-4,6-dione ... Key words: Methyleneketene, 5-methylene-1,3-dioxan-4,6-dione, Cycloaddition, Region-selectivity, Reaction mechanism ... Methyleneketene,5-methylene-1,3-dioxan-4,6-dione,Cycloaddition,Region-selectivity,Reaction mechanism ... Theoretical Study on the Mechanism of the Cycloaddition Reactions Between Methyleneketene and 5-methylene-1,3-dioxan-4,6-dione ...
1,3-Dipolar [3 + 2] cycloaddition reactions of N,C,C-trisubstituted nitrones with ring-acceptor methylenecyclopropanes: a...
... to delineate the factors responsible for the regioselectivity of these class of reactions. The energetics of the reaction of ... For the reactions of N,C,C-trisubstituted nitrone with vicinal ester (-CO2CH3)-substituted methylenecyclopropane (-R1=H, -R2=Ph ... However, it is also clear from the energetics that these reactions are not reversible and are therefore under kinetic control. ... Therefore the selectivity of the reactions is governed solely by the difference in activation barriers leading to the two ...
Intermolecular cycloaddition reactions of exocyclic nitrones facile synthesis of 1-azaspirocycles<...
Intermolecular cycloaddition reactions of exocyclic nitrones facile synthesis of 1-azaspirocycles. Raymond L. Funk, Joy Umstead ... Intermolecular cycloaddition reactions of exocyclic nitrones facile synthesis of 1-azaspirocycles. / Funk, Raymond L.; Daggett ... Intermolecular cycloaddition reactions of exocyclic nitrones facile synthesis of 1-azaspirocycles. Heterocycles. 1987 Aug 1;26( ... Intermolecular cycloaddition reactions of exocyclic nitrones facile synthesis of 1-azaspirocycles. In: Heterocycles. 1987 ; Vol ...
Stereoselective Iodine Atom Transfer [3 + 2] Cycloaddition Reaction with Alkenes Using Unsymmetrical Allylated Active Methine...
Kitagawa O, Miyaji S, Sakuma C, Taguchi T. Stereoselective Iodine Atom Transfer [3 + 2] Cycloaddition Reaction with Alkenes ... Kitagawa, O, Miyaji, S, Sakuma, C & Taguchi, T 2004, Stereoselective Iodine Atom Transfer [3 + 2] Cycloaddition Reaction with ... Kitagawa, O., Miyaji, S., Sakuma, C., & Taguchi, T. (2004). Stereoselective Iodine Atom Transfer [3 + 2] Cycloaddition Reaction ... Dive into the research topics of Stereoselective Iodine Atom Transfer [3 + 2] Cycloaddition Reaction with Alkenes Using ...
Pericyclic Reactions - libvolume6.xyzlibvolume6.xyz/.../pericyclicreactionstutorial2.pdf · Three most common types of...
Venue will be intimated later All four topics of Organic Three Classes of Organic Reactions Polar reactions… ... Pericyclic Reactions Class test on 10/02/07 (3:30 PM to 4:30 PM) ... Cycloaddition reactions. Why does maleic anhydride react easily ... Chapter 6: Reactions of Alkenes: Addition Reactions · PDF fileChapter 6: Reactions of Alkenes: Addition Reactions ... 6.8: Free ... Electrocyclic Reactions. These reactions are defined as involving the cyclization of an n pi-electronsystem to an (n-2)pi + ...
Unveiling [3 + 2] Cycloaddition Reactions of N-Methyl-C-3-Bromophenyl-Nitrone to Dimethyl Maleate: Molecular Electron Density...
... cycloaddition reactions, electron localization function Abstract. Abstract. The zwitterionic-type (zw-type) [3+2] cycloaddition ... Unveiling [3 + 2] Cycloaddition Reactions of N-Methyl-C-3-Bromophenyl-Nitrone to Dimethyl Maleate: Molecular Electron Density ... Cycloaddition Reactions Towards Styrene with a Molecular Electron Density Theory Perspective , Journal of the Mexican Chemical ... These exergonic 32CA reactions have negative Gibbs free energy along the endo and exo stereochemical pathways. The endo ...
Peer Review of Master Organic Chemistry
Present and explain cycloaddition reactions. Target Student Population:. This material would be very useful for an introductory ... give an in-depth overview of substitution and elimination reactions 5. Teach, in detail, about the 4 reaction types: additon, ... The site seeks to 1. aid Organic I students with the transition from G-Chem to O-Chem 2. Present the most prevalent reactions ... electronic flashcards for reactions and free downloads of summary sheets for different organic concepts. Although the blog and ...
Lecture: Lec 3 - Introduction to Limits - DnaTube.com - Scientific Video and Animation Site
Pericyclic Reactions - Paperback - Ian Fleming - Oxford University Press
... including such commercially important synthetic reactions as the Diels-Alder reaction. Reactions such as these are ... This primer reviews these reactions in order to explain their theoretical basis via correlation diagrams. ... Pericyclic reactions constitute a major strand of organic chemistry, ... 2. Cycloaddition reactions. 3. The Woodward-Hoffmann rules and molecular orbitals. 4. Electrocyclic reactions. 5. Sigmatropic ...
Rapid assembly of complex cyclopentanes employing chiral, α,β-unsaturated acylammonium intermediates | Nature Chemistry
Moyano, A. & Ramon Rios, R. Asymmetric organocatalytic cyclization and cycloaddition reactions. Chem. Rev. 111, 4703-4832 (2011 ... al. Horner-Wadsworth-Emmons reaction: use of lithium chloride and an amine for base-sensitive compounds. Tetrahedron Lett. 25, ... Grondal, C., Jeanty, M. & Enders, D. Organocatalytic cascade reactions as a new tool in total synthesis. Nature Chem. 2, 167- ... Jorg, H. The Pauson-Khand reaction in the synthesis of pharmacologically active compounds. Curr. Org. Chem. 14, 1139-1152 (2010 ...
BRINGING THE 4TH DIMENSION TO CHEMICAL CRYSTALLOGRAPHY - TI ME RESOLVED PHOTOCYSTALLOGRAPHY - Research output - the...
Kamaldeep Sharma - Publikationer
- Aalborg Universitets forskningsportal
Cycloaddition Reactions. Chopra, R., Sharma, K., Kumar, M. & Bhalla, V., 5 feb. 2016, I: The Journal of Organic Chemistry. 81, ... Catalytic Hydrothermal Liquefaction of Eucalyptus: Effect of Reaction Conditions on Bio-oils Properties.. Seehar, T. H., Sharma ... An active photocatalyst for Suzuki and Suzuki type coupling reactions. Sharma, K., Kumar, M. & Bhalla, V., 14 aug. 2015, I: ... Potential photocatalysts for the Suzuki and Suzuki type coupling reactions. Singh, G., Kumar, M., Sharma, K. & Bhalla, V., 1 ...
Stereodivergent total synthesis of rocaglaol initiated by synergistic dual-metal-catalyzed asymmetric allylation of benzofuran...
Asymmetric cycloaddition and cyclization reactions catalyzed by chiral N,N′-dioxide-metal complexes. ... Asymmetric synthesis of oxa-bridged oxazocines through a catalytic RhII/ZnII relay [4+3] cycloaddition reaction. ... Synergistic Pd/amine-catalyzed stereodivergent hydroalkylation of 1,3-dienes with aldehydes: reaction development, mechanism, ... Synergetic iridium and amine catalysis enables asymmetric [4+2] cycloadditions of vinyl aminoalcohols with carbonyls. ...
Organic Chemistry/Alkenes - Wikibooks, open books for an open world
Diels-Alder Reaction[edit , edit source]. The Diels-Alder reaction is a reaction (specifically, a cycloaddition) between a ... E1 reactions, like SN1 reactions are 2-step reactions. Also like SN1 reactions, the rate-limiting step is the dissociation of ... On the other hand, E2 reactions, like SN2 reactions are 1-step reactions. And again, as with SN2 reactions, the rate limiting ... The Diels-Alder reaction is the most important example of cycloaddition. Since reaction involves a system of 4 π electrons (the ...
BJOC - [3 + 2] Cycloaddition with photogenerated azomethine ylides in β-cyclodextrin
3 + 2] Cycloaddition with photogenerated azomethine ylides in β-cyclodextrin ... Furthermore, it is anticipated that the addition of H2O quenches the cycloaddition reaction due to a faster reaction of AMY ... Cycloaddition Reactions in Organic Synthesis; WILEY-VCH: Weinheim, 2002. doi:10.1002/3527600256 Return to citation in text: [1 ... β-CD affected the cycloaddition reaction of photogenerated AMY with AN. Upon irradiation of 2 with AN in the presence of β-CD, ...
FARMACIA Y BIOQUIMICA - Research output - San Luis Gonzaga National University of Ica
Cas 1119-51-3|5-Bromo-1-pentene|lookchem
As we report, the Co-mediated pentadienyl/alkyne [5 + 2] cycloaddition reaction generates kinetically stable η2,η3- ... Cobalt-Mediated η5-Pentadienyl/Alkyne [5 + 2] Cycloaddition Reactions: Substitution Effects, Bicyclic Synthesis, and ... exploring substituent effects and extending the reaction to tandem cycloaddition/nucleophilic cyclizations, generating fused ... 3SnLi reactions proceed stereospecifically with inversion at carbon, while the (CH3)3SnLi reactions are nonstereospecific, as ...
Kana M. Sureshan - American Chemical Society
Molecules | Free Full-Text | Structural Determinants of Alkyne Reactivity in Copper-Catalyzed Azide-Alkyne Cycloadditions
... reactions. In previous works, we have identified chelating azides, in particular 2-picolyl azide, as ... our initial effort in identifying azide/alkyne pairs for optimal reactivity in copper-catalyzed azide-alkyne cycloaddition ( ... The reaction mixture was stirred under air for 18 h. After the reaction finished, the reaction mixture was diluted with ethyl ... Scheme 1. Reaction used in the 1H-NMR time course assay to evaluate alkynes. The actual concentrations of reaction ingredients ...
College of Science & Engineering - Research output
- [email protected]
KAKEN - Research Projects | Addition Reaction of Unique Aromatic Ring Systems and Their Ring Transformation and Tribological...
... various cycloaddition reactions were tried and successful results were obtained. In 1,3-dipolar cycloaddition, the reaction ... Publications] H.Ishida: Cycloaddition Reaction of [60]Fullerene with 3,4-Fused Pyrrolo-3-sulfoleneSynlett. 296-299 (2001). * ... Publications] H.Ishida: Cycloaddition Reaction of [60] Fullerene with 3,4-Fused Pyrrolo-3-sulfoleneSynlett. 296-299 (2001). * ... Publications] H.Ishida: Cycloaddition Reaction of C60 with 2-Diazo-1,3-dithiane and Oxidation of the Cycloadduct to Sulfoxide ...
Vauthey Research Group - Group Members
Jos Luis Mascare as Synthetic Strategies Based on Metal-Catalyzed Cyclizations and Cycloaddition Reactions. ... G. Vijay Nair Novel C-C and C-Heteroatom Bond-Forming Reactions Mediated by Nucleophilic Heterocyclic Carbenes (NHCs) and other ... Walter Leitner Green Solvents for Catalysis - From Molecular Understanding to Reaction Engineering Concepts. ... Nicos A. Petasis Elements for Discovery: From New Reactions to New Bioactive Molecules. ...
Staff listing - The University of Nottingham
Steric and Electronic Control of 1, 3-dipolar Cycloaddition Reactions in Carbon Nanotube Nanoreactors The Journal of Physical ... Recyclable glucose-derived palladium(0) nanoparticles as in situ-formed catalysts for cross-coupling reactions in aqueous media ... Glucose-derived palladium (0) nanoparticles as in situ-formed catalysts for Suzuki-Miyaura cross-coupling reactions in ... the role of migration and coalescence in nanocatalyst sintering during the Suzuki-Miyaura reaction Nanoscale. 10(40), 19046- ...
ICMAB - 2013
First diastereoselective [3+2] cycloaddition reaction of diethyl isocyanomethylphosphonate and maleimides. (2013) Organic & ... Bronsted acid-base reactions with anhydrous sulfamates as a pathway to [SO3N]3--containing compounds: Preparation of Li3SO3N ... Detection of different oxidation states of individual manganese porphyrins during their reaction with oxygen at a solid/liquid ... Boosted CO2 reaction with methanol to yield dimethyl carbonate over Mg-Al hydrotalcite-silica lyogels ...
Publications Archives - Page 29 of 29 - The Davies Group
8. [3 + 4] Cycloaddition reactions of vinyl carbenoids with furans. Authors: Huw M.L. Davies, David M. Clark, Thuy K. Smith ... Continue reading "8. [3 + 4] Cycloaddition reactions of vinyl carbenoids with furans" ... 7. Synthesis and reactions of some 1-substituted 1,2-diazetidinones. Authors: Edward C. Taylor , Huw M. L. Davies ... Continue reading "3. Rhodium(II) acetate-catalyzed reaction of ethyl 2-diazo-3-oxopent-4-enoates: Simple routes to 4-aryl-2- ...
SynthesisAzide-Alkyne CycloadditionsNitroneIntramolecularDiels-Alder ReCatalysisNucleophilicAsymmetricNitronesStereoselectivityMechanismReversibleChemistryReactivityKineticsCatalystElectronRadical additionCleavageMoleculesCalculationsAlkynesFormalConjugationCopperOrganocatalyticTechniqueSubstratesComplexesBased on frontierTransitionChemicalSubstituentsIntermediateReactantsMechanismsShownEliminationApplicationTheoreticalActivation barriersPreparationDomino
Synthesis12
- Funk, RL & Daggett, JU 1987, ' Intermolecular cycloaddition reactions of exocyclic nitrones facile synthesis of 1-azaspirocycles ', Heterocycles , vol. 26, no. 8, pp. 2175-2182. (elsevier.com)
- It also shows students how to recognize the different types of pericyclic reaction, their mechanisms, and their applications to organic synthesis. (oup.com)
- Jorg, H. The Pauson-Khand reaction in the synthesis of pharmacologically active compounds. (nature.com)
- Cycloadditions are highly useful reactions in organic synthesis providing complex cyclic structures from easily available precursors [1,2] . (beilstein-journals.org)
- We became interested in the application of photochemical H-abstraction reactions initiated by phthalimides in organic synthesis [14,15] . (beilstein-journals.org)
- Publications] H.Ishida: 'Synthesis of Dicarboxylic acid Derivatives of [60]Fullerene Using Diels-Alder Reaction with Bis(methylene)butanedioates'Tetrahedron Letters. (nii.ac.jp)
- Investigations into the use of the intramolecular Diels-Alder furan cycloaddition (IMDAF) reaction for synthesis of complex polycyclic compounds were carried out. (hud.ac.uk)
- Copper-catalysed N-arylation of oxindole with 2-bromofuran delivered a potentially useful intermediate for the picrinine synthesis, containing diene and all necessary tether atoms for the cycloaddition. (hud.ac.uk)
- Intermolecular [2+2] reaction of N-allenylsulfonamides with vinylarenes: enantioselective gold(i)-catalyzed synthesis of cyclobutane derivatives. (semanticscholar.org)
- 2] This reaction has also been applied to the racemic synthesis of aza-oxindoles. (rsc.org)
- A versatile route for the synthesis of highly functionalized, polyanionic macromolecules based on dendritic polyglycerol was applied by means of the Huisgen-Sharpless-Meldal 1,3-dipolar cycloaddition ("click-reaction") of polyglycerolazide precursors and alkyne-functionalized anions such as sulfonates, carboxylates, phosphonates, and bisphosphonates. (fu-berlin.de)
- The structure of 192 was confirmed by the synthesis of methyl 2,6-dimethylpyridine-3-carboxylate (195), the opposite regioisomer.The synthesis of methyl 3,5-dimethylpyridine-2-carboxylate (199) from [4+2] cycloaddition of 2-methyl-2-propenal dimethylhydrazone (171) and 16 is described. (ndltd.org)
Azide-Alkyne Cycloadditions1
- 2011) Reliable and Efficient Procedures for the Conjugation of Biomolecules through Huisgen Azide-Alkyne Cycloadditions. (jenabioscience.com)
Nitrone5
- The energetics of the reaction of the phenyl-substituted nitrone with unsubstituted methylenecyclopropane indicate that the formation of the 5-spirocyclopropane is favored over the 4-spirocyclopropane kinetically and thermodynamically. (springeropen.com)
- However, the energetics of the reaction of the same phenyl nitrone with vicinal ester (-CO 2 CH 3 )-substituted methylenecyclopropane show an inversion in the regioselectivity favoring the formation of the 4-regioisomer over the 5-regioisomer. (springeropen.com)
- 2003 ) performed a theoretical study at the DFT B3LYP/6-31G(d) theory level on the 1,3-dipolar cycloaddition reactions of C -(methoxycarbonyl)- N -methyl nitrone with methyl acrylate and vinyl acetate with the aim of defining the preferred approaches for cycloaddition reactions of nitrones and to introduce additional details in the commonly accepted general model of 1,3-dipolar cycloaddition of nitrones. (springeropen.com)
- The zwitterionic -type ( zw- type) [3+2] cycloaddition (32CA) reactions of N-methyl-C-3-bromophenyl-nitrone 1 with dimethyl maleate 2 with increased electrophilicity were investigated using the Molecular Electron Density Theory (MEDT) at the MPWB95/6-311++G(d,p) computational level. (jmcs.org.mx)
- The associated zw -type 32CA reactions are accelerated due to the high nucleophilic character of N-methyl-C-3-bromophenyl-nitrone 1 and the strong electrophilic character of dimethyl maleate 2 , which also play a critical part in the mechanism of the reaction, influencing the stereoselectivity, with activation enthalpies in between 34.04 and 38.37 kJ.mol -1 in the gas phase. (jmcs.org.mx)
Intramolecular1
- Reaction with a nerve agent is followed by a rapid intramolecular cyclization that creates a new fluorophore and destroys the agent. (scripps.edu)
Diels-Alder Re3
- Pericyclic reactions constitute a major strand of organic chemistry, including such commercially important synthetic reactions as the Diels-Alder reaction. (oup.com)
- Publications] H.Ishida: 'Diels-Alder Reaction of [60]Fullerene with Cyclooctatetraene and Electrophilic Addition to the Cycloadduct'Tetrahedron Letters. (nii.ac.jp)
- These were synthesized by Diels-Alder reaction of corresponding p-quinones and acyclic-1,3-dienes [diagram omitted]. (ndltd.org)
Catalysis3
- Herein, I will discuss the breaking of C-S and C-F bonds for the generation of C-centred radicals and its application in C-C bond forming reactions using photoredox catalysis and visible light. (beilstein-institut.de)
- This arrangement allows isolation and direct observation of reactive intermediates and catalysis of reactions with large rate enhancements. (scripps.edu)
- The [2 + 2 + 2] cycloaddition of 1,5-bisallenes and alkynes under the catalysis of Rh(I) with hemilabile thioether-functionalized N-heterocyclic carbene ligands is described. (bvsalud.org)
Nucleophilic2
- Apart from these cycloaddition, radical and nucleophilic additions aided with inorganic reagents were attempted. (nii.ac.jp)
- Novel elastomers are being developed by nucleophilic substitution and cycloaddition reactions of commercial materials such as halogenated butyl rubber and polybutadiene. (queensu.ca)
Asymmetric3
- Bui, T. & Barbas, C. F. III A proline-catalyzed asymmetric Robinson annulation reaction. (nature.com)
- Studies were begun towards an alternative approach, where the reversible cycloaddition is coupled to an irreversible asymmetric transformation in a dynamic kinetic resolution process. (hud.ac.uk)
- Under the guidance of Professor Armido Studer, he focused on catalytic asymmetric cycloaddition reactions. (beilstein-institut.de)
Nitrones3
- 1,3-Dipolar [3 + 2]-cycloaddition of nitrones to the carbon-carbon double bonds of methylenecyclopropanes yields a mixture of regioisomeric 4- and 5-isoxazolidines. (springeropen.com)
- The mechanisms of the reactions of N , C , C -trisubstituted nitrones with ring acceptor substituted dimethyl methylenecyclopropanes-1,2-dicarboxylate and aryl methylidene cyclopropanes-1,1-dicarboxylate have been investigated with the Becke 3-Parameter Lee-Yang-Par exchange-correlation functional, a Hartree-Fock DFT hybrid functional, to delineate the factors responsible for the regioselectivity of these class of reactions. (springeropen.com)
- 1,3-Dipolar [3 + 2]-cycloaddition of nitrones to the carbon-carbon double bonds of methylenecyclopropanes yields a mixture of regioisomeric 4- and 5-isoxazolidines that are very useful due to their versatility, stereochemistry and their biological activities (Li et al. (springeropen.com)
Stereoselectivity2
- Treatment of 1-diethylphosphonyl- or 1-phenyl-sulfonyl-2-(iodomethyl)cyclopropane-l-carboxylate with Et 3 B leads to an unsymmetrical allylated active methine radical species that gives functionalized cyclopentane derivatives with high stereoselectivity through iodine atom transfer [3 + 2] cycloaddition reaction with alkenes. (elsevier.com)
- Stereoselectivity in photochemical reactions can be achieved by use of supramolecular chemistry [36,37] . (beilstein-journals.org)
Mechanism5
- Theoretical Study on the Mechanism of the Cycloaddition Reactions Between Methyleneketene and 5-methylene-1,3-dioxan-4,6-dione[J].Acta Phys. (pku.edu.cn)
- New Research Progress of the Electrochemical Reaction Mechanism, Preparation and Modification for LiFePO 4 [J]. Acta Phys. (pku.edu.cn)
- Does the mechanism involve a [2+2] cycloaddition (shown above) or a 1,2-insertion reaction? (hmc.edu)
- Furthermore, the reactions between these CIs, and H 2 O and SO 2 may serve as the dominant mechanism for removing the former from the troposphere, thereby determining the atmospheric CI concentrations. (aaqr.org)
- The reaction follows a typical [2 + 2 + 2] cycloaddition mechanism. (bvsalud.org)
Reversible2
- However, it is also clear from the energetics that these reactions are not reversible and are therefore under kinetic control. (springeropen.com)
- The reactions are reversible. (fdocument.org)
Chemistry7
- The website itself features e-mail alerts, links to other popular chemistry sites such as Kahn Academy, study strategies, electronic flashcards for reactions and free downloads of summary sheets for different organic concepts. (merlot.org)
- The click reaction that changed chemistry: Azides and alkynes react very efficiently when copper ions are added. (cosmosmagazine.com)
- This reaction was fast and efficient, but at the advent of click chemistry, it lacked precision and often needed strict requirements to work. (cosmosmagazine.com)
- It's become a tremendously common reaction in chemistry. (cosmosmagazine.com)
- This discovery led to Bertozzi's development of 'bioorthoganal' chemistry, or reactions that happen on the surface of a cell without disrupting the cell's behaviour. (cosmosmagazine.com)
- 2001) Click chemistry: diverse chemical function from a few good reactions. (jenabioscience.com)
- 2009) Click Chemistry and Bioorthogonal Reactions: Unprecedented Selectivity in the Labeling of Biological Molecules. (jenabioscience.com)
Reactivity3
- Both reactivity and selectivity are rationalized in relation to the polarity of the reaction. (jmcs.org.mx)
- Irradiation of [email protected]β-CD in the presence of AN in aqueous solution where cycloadduct 7 was formed highly suggests that decarboxylation and [3 + 2] cycloaddition take place in the ternary complex, whereas such a reactivity from bulky adamantane 3 is less likely. (beilstein-journals.org)
- This work represents our initial effort in identifying azide/alkyne pairs for optimal reactivity in copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions. (mdpi.com)
Kinetics3
- We study these reactions by variable temperature one- and two-dimensional NMR spectroscopy, kinetics experiments, and theoretical modeling. (hmc.edu)
- Research projects range from studies of the structure-property relationships of new materials to detailed analyses of reaction kinetics and selectivity. (queensu.ca)
- This study, however, reports on the generation and reaction kinetics of larger CIs, which have been shown to oxidize NO and SO 2 into NO 2 and SO 3 , respectively, leading to the production of nitric acid and sulfuric acid. (aaqr.org)
Catalyst1
- One pot catalytic syntheses of substituted 1,8-naphthyridines and 2 H -pyrano[3,2- g ]quinolin-2-ones by the reaction of α-ketoalkynes with 6-aminonicotinamide and 7-amino-4-methylcoumarin respectively in water, using a homogeneous nickel catalyst at very mild reaction conditions are described. (heterocycles.jp)
Electron3
- They are all concerted reactions, electron reorganization takes place in single step. (fdocument.org)
- These reactions are defined as involving the cyclization of an n pi-electronsystem to an (n-2)pi + 2sigma-electron system or the reverse process. (fdocument.org)
- [12] . Photochemical reactions of phthalimides include H-abstractions, cycloadditions and photoinduced electron transfer (PET) [13] . (beilstein-journals.org)
Radical addition1
- An efficient CuCl/bpy-mediated atom transfer radical addition reaction of styrenes with CF 3 CHCl 2 and CF 3 CCl 3 is developed. (sioc-journal.cn)
Cleavage1
- A highly stereoselective synthetic route to the title compound was explored by featuring the [2+2]-cycloaddition reaction of chlorosulfonyl isocyanate with the 4H-1,3-dioxin derivative readily obtainable from methyl (R)-3-hydroxybutyrate, the Baeyer-Villiger reaction resulting in novel cleavage of the acetal moiety, and the Reformatsky reaction with sterically crowded 3-(2-bromopropionyl)-2-oxazolidone derivatives. (elsevier.com)
Molecules3
- This reaction is now used globally to link molecules together in a simple manner. (cosmosmagazine.com)
- The capsules reveal the behavior of molecules in very small spaces and channel their reactions along previously unknown pathways. (scripps.edu)
- Synthetic organic reactions that use reactions between unsaturated molecules to form cyclical products. (bvsalud.org)
Calculations1
- The regio-selectivity of the reactions observed by experiments was correctly predicted by the calculations. (pku.edu.cn)
Alkynes1
- In the current work, two types of alkynes are shown to undergo rapid CuAAC reactions under both copper(II)- (via an induction period) and copper(I)-catalyzed conditions. (mdpi.com)
Formal1
- Formal [4 + 2] cycloaddition of donor-acceptor cyclobutanes and aldehydes: stereoselective access to substituted tetrahydropyrans. (semanticscholar.org)
Conjugation1
- The fact that oxidation, as one of the main routes of phase I metabolism of drugs, follows by conjugation reactions, and also formation of nitrenium ion as one of the clozapine oxidation products, directed us to investigate the oxidation of clozapine (CLZ) in the presence of nucleophile. (researchgate.net)
Copper2
- In 2002, Sharpless and Morten Meldal, independently of each other, developed an elegant and efficient chemical reaction: the copper catalysed azide-alkyne cycloaddition. (nobelprize.org)
- 1] During these studies, they discovered a novel and efficient route to access racemic 3,3,-disubstituted oxindoles which employed a copper-mediated radical reaction. (rsc.org)
Organocatalytic1
- His area of research mainly focused on new organocatalytic cascade reactions. (beilstein-institut.de)
Technique1
- All the geometries of the stationary points on the reactions path have been optimized by energy gradient technique, and all transition states were characterized by vibration frequency analysis. (pku.edu.cn)
Substrates2
Complexes2
- We found out that H-abstraction reactions were about ten times more efficient in the β-CD complexes than in the isotropic solution, and the macrocyclic host affected the stereochemistry of the reaction. (beilstein-journals.org)
- Cycloparaphenylene Metal Complexes and New Metal Carbonyl Coupling Reactions. (ncsu.edu)
Based on frontier1
- An analysis based on frontier molecular orbital theory shows that the reaction mechanisms correspond to [4+2] description. (pku.edu.cn)
Transition3
- The results can be summed up as follows: the cycloaddition of different double bond of methyleneketene with 5-methylene- 1,3-dioxan-4,6-dione are all concerted but nonsynchrorous, taking place through twisted transition states. (pku.edu.cn)
- Reactions such as these are characterised by their predictable stereochemistry and cyclic transition structures. (oup.com)
- These have been prepared in a variety of shapes and sizes, from those appropriate for encapsulation of methane to those capable of encapsulating transition states of cycloaddition reactions. (scripps.edu)
Chemical3
- Between them and their groups, the researchers developed an elegant series of reactions that get used everywhere in chemical manufacture, and have been particularly helpful in making pharmaceuticals, mapping DNA and developing cancer treatments. (cosmosmagazine.com)
- 2010) Cu-free click cycloaddition reactions in chemical biology. (jenabioscience.com)
- Bioorthogonal modifications and cycloaddition reactions for RNA chemical biology. (mpg.de)
Substituents2
- Substrate d has gem-dialkyl substituents which should allow our catalytic reaction to occur at a lower temperature. (hmc.edu)
- Three substituent-dependent types of reactions were observed: (1) for adducts possessing hydrogen substituents at C₄a and C₈a (bridgehead position), the prevalent process was one of abstraction of a β-hydrogen atom from C₅(or equivalently, C₈) by excited carbonyl oxygen. (ndltd.org)
Intermediate1
- The same type of cycloaddition with 3,4-fused pyrrolosulfolene unusually afforded a cycloadduct originating from direct trap of 3,4-dimethylenepyrrole intermediate, and this may reflect high radicophilicity of [60]fullerene. (nii.ac.jp)
Reactants1
- 2004 ). Regioselectivity of 1,3-dipolar cycloaddition reactions in general is determined by electronic structure of reactants, steric factors or combination of both (Jones and Martin 2002 ). (springeropen.com)
Mechanisms2
- Crystal Structures, Reaction Mechanisms, and Optimization Strategies of MnO 2 Cathode for Aqueous Rechargeable Zinc Batteries [J]. Acta Phys. (pku.edu.cn)
- Reaction Mechanisms in the Thermal Decomposition of CL-20 Revealed by ReaxFF Molecular Dynamics Simulations [J]. Acta Phys. (pku.edu.cn)
Shown2
- The reactions have even been shown to work in living mice. (cosmosmagazine.com)
- It was shown that under the reaction conditions, oxidation of the product to the corresponding isatin was a competing side reaction, an important observation for future optimisation of this reaction. (hud.ac.uk)
Elimination2
- give an in-depth overview of substitution and elimination reactions 5. (merlot.org)
- The rate of an elimination reaction is increased by more than three decades through distortions induced by binding at a remote site. (heterocycles.jp)
Application1
- 2007) The Rise of Azide-Alkyne 1,3-Dipolar 'Click' Cycloaddition and its Application to Polymer Science and Surface Modification. (jenabioscience.com)
Theoretical1
- This primer reviews these reactions in order to explain their theoretical basis via correlation diagrams. (oup.com)
Activation barriers1
- Therefore the selectivity of the reactions is governed solely by the difference in activation barriers leading to the two isomers and not in any way by the thermodynamic stability of the isomers formed. (springeropen.com)
Preparation1
- Research projects in this area range from "blue-sky" methods of improving reaction selectivity to product engineering exercises focused on the preparation of polyolefin nanocomposites for advanced automotive applications. (queensu.ca)
Domino1
- Pellissier, H. Stereocontrolled domino reactions. (nature.com)