Relevant bibliographies by topics / Diels-Alder cycloaddition reactions

Academic literature on the topic 'Diels-Alder cycloaddition reactions'

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Published: 17 July 2024

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Journal articles on the topic "Diels-Alder cycloaddition reactions"

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Grygorenko, Oleksandr O., Viktoriia S. Moskvina, Oleksandr V. Hryshchuk, and Andriy V. Tymtsunik. "Cycloadditions of Alkenylboronic Derivatives." Synthesis 52, no. 19 (June 24, 2020): 2761–80. http://dx.doi.org/10.1055/s-0040-1707159.

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The literature on cycloaddition reactions of boron-containing alkenes is surveyed with 132 references. The data are categorized according to the reaction type ([2+1], [2+2], [3+2], [4+2], and [4+3] cycloadditions). The cyclopropanation and the Diels–Alder reactions of alkenylboronic derivatives have been studied more or less comprehensively, and for some substrates, they can be considered as convenient methods for the rapid regio- and stereoselective construction of even complex cyclic systems. Other types of the cycloadditions, as well as mechanistic aspects of the processes, have been addressed less thoroughly in the previous works.1 Introduction2 [2+1] Cycloaddition2.1 Cyclopropanation2.1.1 With Methylene Synthetic Equivalents2.1.2 With Substituted Carbenoids2.2 Epoxidation2.3 Aziridination3 [2+2] Cycloaddition4 [3+2] Cycloaddition4.1 With Nitrile Oxides4.2 With Diazoalkanes4.3 With Nitrones4.4 With Azomethine Ylides5 [4+2] Cycloaddition6 [4+3] Cycloaddition7 Conclusions and Outlook
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Burnell, D. Jean, and Zdenek Valenta. "π-Facial stereoselectivity in the Diels–Alder reactions of a rigid carbocyclic diene: spiro(bicyclo[2.2.1]heptane-2,1′-[2,4]cyclopentadiene)." Canadian Journal of Chemistry 69, no. 1 (January 1, 1991): 179–84. http://dx.doi.org/10.1139/v91-028.

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The plane-nonsymmetrical diene spiro(bicyclo[2.2.1]heptane-2,1′-[2,4]cyclopentadiene) (2) was synthesized, and the π-facial stereoselectivity of its Diels–Alder cycloadditions with three cyclic dienophiles was examined. Adduct ratios were very similar, and the selectivity is surmised to be mainly the result of steric interactions at the transition state. Key words: facial stereoselectivity, Diels–Alder, cycloaddition.
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Soares, Maria I. L., Ana L. Cardoso, and Teresa M. V. D. Pinho e Melo. "Diels–Alder Cycloaddition Reactions in Sustainable Media." Molecules 27, no. 4 (February 15, 2022): 1304. http://dx.doi.org/10.3390/molecules27041304.

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Diels–Alder cycloaddition reaction is one of the most powerful strategies for the construction of six-membered carbocyclic and heterocyclic systems, in most cases with high regio- and stereoselectivity. In this review, an insight into the most relevant advances on sustainable Diels–Alder reactions since 2010 is provided. Various environmentally benign solvent systems are discussed, namely bio-based derived solvents (such as glycerol and gluconic acid), polyethylene glycol, deep eutectic solvents, supercritical carbon dioxide, water and water-based aqueous systems. Issues such as method’s scope, efficiency, selectivity and reaction mechanism, as well as sustainability, advantages and limitations of these reaction media, are addressed.
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Zhou, You-Yun, and Christopher Uyeda. "Catalytic reductive [4 + 1]-cycloadditions of vinylidenes and dienes." Science 363, no. 6429 (February 21, 2019): 857–62. http://dx.doi.org/10.1126/science.aau0364.

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Cycloaddition reactions provide direct and convergent routes to cycloalkanes, making them valuable targets for the development of synthetic methods. Whereas six-membered rings are readily accessible from Diels-Alder reactions, cycloadditions that generate five-membered rings are comparatively limited in scope. Here, we report that dinickel complexes catalyze [4 + 1]-cycloaddition reactions of 1,3-dienes. The C1partner is a vinylidene equivalent generated from the reductive activation of a 1,1-dichloroalkene in the presence of stoichiometric zinc. Intermolecular and intramolecular variants of the reaction are described, and high levels of asymmetric induction are achieved in the intramolecular cycloadditions using aC2-symmetric chiral ligand that stabilizes a metal-metal bond.
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Zezula, Josef, Tomáš Hudlický, and Ion Ghiviriga. "Intramolecular Diels-Alder Cycloadditions of cis-Cyclohexadienediols Derived Enzymatically from (2-Azidoethyl)benzene. Construction of Highly Functionalized Bridged Isoquinoline Synthons." Collection of Czechoslovak Chemical Communications 66, no. 8 (2001): 1269–86. http://dx.doi.org/10.1135/cccc20011269.

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(3aR,7aS)-4-(2-Azidoethyl)-2,2-dimethyl-3a,7a-dihydrobenzo[1,3]dioxole (22) was converted in two steps to trienes23and24, which upon heating underwent intramolecular Diels-Alder reactions to give mixtures of isomeric 11,11-dimethyl-5-oxo-10,12-dioxa-4-azatetracyclo[6.5.2.01,6.09,13]pentadec-14-ene-7-carboxylates25,26and27,28, respectively. These products were separated and identified. For comparison, intermolecular Diels-Alder cycloaddition of diene22with maleic anhydride was carried out. Products of this reaction, 1-(2-azidoethyl)-4,4-dimethyl-3,5,10-trioxatetracyclo[5.5.2.02,6.08,12]tetradec-13-ene-9,11-diones (29and30) were converted to methyl ester analogues of31and32in a two-step sequence. The stereochemical outcome of these cycloadditions is discussed as well as their possible utilization in organic synthesis, especially in total synthesis of some alkaloids.
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Pratt, Andrew J., Phillip M. Rendle, and Peter J. Steel. "Anticancer Prodrug Studies: Diels - Alder Chemistry of 1-Methylthio-1-(p-tolylsulfonyl)ethene." Australian Journal of Chemistry 64, no. 7 (2011): 945. http://dx.doi.org/10.1071/ch10450.

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The reactivity of 1-methylthio-1-(p-tolylsulfonyl)ethene (1) as a dienophile in Diels–Alder chemistry is investigated. Cycloaddition reactions were carried out with a range of pyran-2-ones and isobenzofurans. The initial Diels–Alder adducts have the potential of undergoing fragmentation in chemistry that is relevant to the design of anticancer intercalator prodrugs. The nature of the final products of the reactions provided insights into both the cycloaddition reactions and fragmentation pathways of the adducts. By comparison with a thioether group, the sulfonyl substituent of the dienophile was found to decrease the reactivity and regioselectivity of the cycloaddition chemistry and to facilitate fragmentation of the initial adducts by the elimination of p-toluenesulfinic acid.
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Carlini, Rina, Kerianne Higgs, Nicholas Taylor, and Russell Rodrigo. "Diels–Alder adducts of ortho-benzoquinones: rearrangements and further transformations." Canadian Journal of Chemistry 75, no. 6 (June 1, 1997): 805–16. http://dx.doi.org/10.1139/v97-097.

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ortho-Benzoquinones substituted with an electron-withdrawing group (EWG = CO2Me, COSMe, COCH3, CHO) at C-3 or C-4 react as dienophiles at the C3—C4 double bond in Diels–Alder reactions with several dienes, with predictable regiochemistry. The adducts undergo migration of the "angular" EWG substituent with concomitant aromatization to produce substituted catechols. The bicyclic products can be oxidized in situ and annelated by a further Diels–Alder reaction to yield 9,10-phenanthraquinone systems. When (2E)-2,4-pentadienol is employed as the diene in the second cycloaddition, reaction of the alcoholic hydroxyl group with one of the quinone carbonyl groups results in the production of tetracyclic lactols 22a, 22b, and 23. Keywords: benzoquinone, Diels–Alder, rearrangement, phenanthraquinone, phenanthrofuran.
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Ayadi, Sameh, and Manef Abderrabba. "Étude DFT des réactions de cycloaddition de type Diels–Alder sur le 4-aza-6-nitrobenzofuroxane." Canadian Journal of Chemistry 85, no. 5 (May 1, 2007): 331–35. http://dx.doi.org/10.1139/v07-026.

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The purpose of this work is a theoretical study of Diels–Alder reactions between the 4-aza-6-nitrobenzofuroxan 1 with a series of dienophiles 3a–3c. From a thermodynamic and orbital point of view, we discuss the reactivity and the stereoselectivty of these reactions. Activation barriers in the Diels-Alder reactions of compound 1 with a series of dienophiles 3a–3c have been calculated and discussed.Key words: inverse electron demand Diels–Alder (IEDDA), DFT method, 4-aza-6-nitrobenzofuroxane.
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Piers, Edward, Richard W. Friesen, Paul Kao, Steven J. Rettig, and James Trotter. "Synthesis of functionalized hexahydro-, octahydro-, and decahydro-1H-phenalenes via Diels–Alder reactions of 1-methylene-4a-methoxycarbonyl-1,2,3,4,4a,5,6,7-octahydronaphthalene and related dienes." Canadian Journal of Chemistry 71, no. 9 (September 1, 1993): 1463–83. http://dx.doi.org/10.1139/v93-188.

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The results of a study of Diels–Alder reactions of the bicyclic dienes 6–8 with a variety of dienophiles are reported. Although 6 and 7 undergo cycloaddition reactions smoothly and efficiently, thermal Diels–Alder reactions of 8 are generally sluggish or, under the conditions investigated, do not proceed at all. Additions of tetracyanoethylene (TCNE) to 6–8 are highly face-selective, with preferential attack of the dienophile on the side of the dienes opposite to the angular methoxycarbonyl group. Reaction of 7 with maleic anhydride (MAN) is completely face-selective and proceeds preferentially via an endo transition state. Diels–Alder reactions of 6 and 7 with methyl acrylate (MAC) and nitroethylene (NE) are entirely regioselective, but the face-selectivities, which vary from ~2:1 to ~3:1, are rather low. The use of this chemistry as a method for the synthesis of functionalized, stereochemically defined, perhydro-1H-phenalenes is demonstrated.
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Kotha, Sambasivarao, Milind Meshram, and Nageswara Panguluri. "Advanced Approaches to Post-Assembly Modification of Peptides by Transition-Metal-Catalyzed Reactions." Synthesis 51, no. 09 (March 25, 2019): 1913–22. http://dx.doi.org/10.1055/s-0037-1612418.

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We have summarized diverse synthetic approaches for the modification of peptides by employing transition-metal-catalyzed reactions. These methods can deliver unusual peptides suitable for peptidomimetics. To this end, several popular reactions such as Diels–Alder, 1,3-dipolar cycloaddition, [2+2+2] cyclotrimerization, metathesis, Suzuki­–Miyaura cross-coupling, and Negishi coupling have been used to assemble modified peptides by post-assembly chemical modification strategies.1 Introduction2 Synthesis of a Cyclic α-Amino Acid Derivative via a Ring-Closing Metathesis Protocol3 Peptide Modification Using a Ring-Closing Metathesis Strategy4 Peptide Modification via a [2+2+2] Cyclotrimerization Reaction5 Peptide Modification by Using [2+2+2] Cyclotrimerization and Suzuki Coupling6 Peptide Modification via a Suzuki–Miyaura Cross-Coupling7 Peptide Modification via Cross-Enyne Metathesis and a Diels–Alder­ Reaction as Key Steps8 Peptide Modification via 1,3-Dipolar Cycloaddition Reactions9 Modified Peptides via Negishi Coupling10 A Modified Dipeptide via Ethyl Isocyanoacetate11 Conclusions
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Dissertations / Theses on the topic "Diels-Alder cycloaddition reactions"

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Chumachenko, Natasha. "[Beta]-acryloyloxysulfonyl tethers for intramolecular Diels-Alder cycloaddition reactions." [Kent, Ohio] : Kent State University, 2005. http://rave.ohiolink.edu/etdc/view?acc%5Fnum=kent1135392557.

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Thesis (Ph.D.)--Kent State University, 2005.
Title from PDF t.p. (viewed July 28, 2005). Author's first name appears on the abstract page as: Nataliya. Advisor: Paul Sampson. Keywords: b-hydroxysulfones; [beta]-hydroxysulfones; epoxide opening; intramolecular Diels-Alder reaction; vinylsulfones. Includes bibliographical references (p.194- 202).
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Chumachenko, Nataliya. "b-Acryloyloxysulfonyl Tethers for Intramolecular Diels-Alder Cycloaddition Reactions." Kent State University / OhioLINK, 2005. http://rave.ohiolink.edu/etdc/view?acc_num=kent1135392557.

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Shengxian, Zhao. "Cycloaddition reactions of meso-tetraarylporphyrins." Doctoral thesis, Universidade de Aveiro, 2005. http://hdl.handle.net/10773/4871.

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Doutoramento em Química
O trabalho apresentado nesta dissertação descreve o comportamento de meso-tetra-arilporfirinas em reacções de ciclo-adição e suas possíveis aplicações na síntese de novas porfirinas com grupos policíclicos aromáticos (“π-extended porphyrins”). No capítulo 1 apresenta-se uma revisão das aplicações de porfirinas e compostos afins e também das reacções de ciclo-adição que envolvem ligações duplas (periféricas) do macrociclo. O capítulo 2 descreve o trabalho feito em reacções de cicloadição 1,3-dipolar de meso-tetra-arilporfirinas com iletos de azometino. Considerou-se primeiramente a reactividade de meso-tetra-arilporfirinas simétricas perante iletos de azometino. Em seguida estudaram-se as reacções de meso-tetra-arilporfirinas de tipo A3B também com iletos de azometino. Seguidamente consideraram-se estudos similares mas desta vez visando reacções de cicloadição 1,3-dipolar, intramolecular, com meso-(o-formilfenil)porfirinas. O capítulo 3 descreve os estudos efectuados sobre transformações de Diels-Alder de meso-tetra-arilporfirinas com orto-quinodimetano de tipo pirazínico. Os novos produtos (“π-extended porphyrins”) obtiveram-se por ciclização intramolecular entre grupos meso-arilo e o anel quinoxalínico fundido em β. No capítulo 4 descrevem-se os estudos de ciclo-adição 1,3-dipolar de iletos N-piridínicos contendo o macrociclo porfirínico. As reacções de tais iletos com quinonas e com acetilenodicarboxilato de dimetilo originaram porfirinas subsituidas em posição meso com grupos de tipo indolizina. Essas quinonas foram usadas em excesso, actuando como dipolarófilos iniciais e depois como oxidantes. Obtiveram-se novos compostos aromáticos policíclicos nas reacções daqueles iletos com alcenos electronicamente deficientes e na ausência de oxidante. O capítulo 5 relata os resultados dos estudos de síntese de porfirinas com grupos policíclicos aromáticos através de reacções electrocíclicas. Isso foi conseguido a partir das reacções de porfirinas contendo grupos cetónicos com iletos de fósforo. A caracterização estrutural destes novos derivados fez-se recorrendo ao uso de técnicas espectroscópicas modernas, especialmente através de estudos de RMN. Estes métodos de RMN incluíram métodos mono e bidimensionais (1D: 1H, 13C, DEPT; 2D: COSY, NOESY, HSQC, HMBC).
The work presented in this dissertation describes the cycloaddition reaction studies concerning meso-tetraarylporphyrins and also their applications in the synthesis of novel π-extended porphyrins. Chapter 1 is a review on the applications of porphyrin derivatives and also on the cycloaddition reactions involving the peripheral double bonds of porphyrins. Chapter 2 is related with the 1,3-dipolar cycloaddition reactions of meso-tetraarylporphyrins with azomethine ylides. Firstly, the reactivities of symmetrical meso-tetraarylporphyrins in the reactions with azomethine ylides were investigated; secondly, the 1,3-dipolar cycloaddition reactions of A3B type meso-tetraarylporphyrins with azomethine ylides were also carried out; thirdly, the intramolecular 1,3-dipolar cycloaddition reactions of meso-(o-formylphenyl)porphyrins were also studied. Chapter 3 is related with Diels-Alder reactions of meso-tetraarylporphyrins with pyrazine ortho-quinodimethane. The novel π-extended porphyrins were obtained from the intramolecular ring closure reactions between the meso-aryl group and the β-fused quinoxaline ring. Chapter 4 is related with 1,3-dipolar cycloaddition reactions of porphyrinic pyridinium N-ylides. The reactions of porphyrinic pyridinium N-ylides with quinones and dimethyl acetylenedicarboxylate afford meso-substituted indolizine porphyrins. The quinones were used in excess, acting as dipolarophiles and as oxidants. The novel polycyclic aromatic compounds were obtained from the reactions of porphyrinic pyridinium N-ylides with the electron-deficient alkenes in the absence of any oxidant. Chapter 5 is related with the synthesis of polycyclic aromatic porphyrin analogues via electrocyclic reactions.These novel analogues were synthesized from the reactions of ketone-bridged porphyrins with phosphorus ylides. For the structural characterizations of the new compounds modern analytical techniques were used, with a special emphasis on NMR spectroscopic studies. These NMR methods include 1D: 1H, 13C, DEPT; 2D: COSY, NOESY, HSQC, HMBC.
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MacNevin, Christopher J. "Reactivity of substituted 4-Pyridones in normal and inverse demand Diels-Alder cycloaddition /." Electronic version (PDF), 2003. http://dl.uncw.edu/etd/2003/macnevinc/christophermacnevin.pdf.

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Nagare, A. S. "Physical - organic aspects of diels - alder reactions in eutectic and other environmental benign media." Thesis(Ph.D.), CSIR-National Chemical Laboratory, Pune, 2016. http://dspace.ncl.res.in:8080/xmlui/handle/20.500.12252/5884.

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Compain-Batissou, Cudel Muriel. "SYNTHESE DE NOUVELLES QUINONES HETEROCYCLIQUES PAR APPLICATION DES REACTIONS DE CYCLOADDITIONS DE DIELS-ALDER ET 1,3-DIPOLAIRE. EVALUATION IN VITRO DE LEUR ACTIVITE SUR TOXOPLASMA GONDII." Phd thesis, Université Claude Bernard - Lyon I, 2007. http://tel.archives-ouvertes.fr/tel-00281991.

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La toxoplasmose est une anthropozoonose ubiquitaire causée par Toxoplasma gondii. Malgré de nombreuses recherches, l'arsenal thérapeutique reste très restreint. L'objectif des travaux présentés dans ce mémoire est la synthèse de carbazolequinones et l'évaluation de leur efficacité sur T. gondii. Les carbazolequinones naturelles comme les calothrixines ont des propriétés antiparasitaires et cytotoxiques. La synthèse de para- et ortho-quinones de type benzo-, isoxazolo- et triazolo-carbazolequinones a été réalisée par application des réactions de cycloaddition [4+2] ou 1,3-dipolaires régiosélectives. La stratégie de synthèse à partir de dipolarophiles monobromés permet en effet, d'accéder sélectivement au régioisomère souhaité. Les attributions de structure des régiosiomères ont été confirmées par RMN 1H NOE et par une étude des corrélations 1H -13C HMBC. Concernant l'évaluation biologique in vitro, les composés inhibent la croissance de T. gondii comme la sulfadiazine et la pyriméthamine, avec une cytotoxicité sur les cellules myélomonocytiques THP1. Aucun des composés synthétisés n'inhibent la PNP, enzyme clé de la voie de sauvetage des purines, seule voie d'accès pour le parasite aux bases puriques. L'inhibition de la croissance de T. gondii par nos composés n'est pas liée directement liée à l'inhibition de la PNP.
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Banert, Klaus, Sandra Bochmann, Andreas Ihle, Oliver Plefka, Florian Taubert, Tina Walther, Marcus Korb, Tobias Rüffer, and Heinrich Lang. "Synthesis with Perfect Atom Economy: Generation of Furan Derivatives by 1,3-Dipolar Cycloaddition of Acetylenedicarboxylates at Cyclooctynes." Universitätsbibliothek Chemnitz, 2014. http://nbn-resolving.de/urn:nbn:de:bsz:ch1-qucosa-152891.

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Cyclooctyne and cycloocten-5-yne undergo, at room temperature, a 1,3-dipolar cycloaddition with dialkyl acetylenedicarboxylates 1a,b to generate furan-derived short-lived intermediates 2, which can be trapped by two additional equivalents of 1a,b or alternatively by methanol, phenol, water or aldehydes to yield polycyclic products 3b–d, orthoesters 4a–c, ketones 5 or epoxides 6a,b, respectively. Treatment of bis(trimethylsilyl) acetylenedicarboxylate (1c) with cyclooctyne leads to the ketone 7 via retro-Brook rearrangement of the dipolar intermediate 2c. In all cases, the products are formed with perfect atom economy.
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Alves, Jessica. "Advanced photochemical reaction systems for molecular design." Thesis, Queensland University of Technology, 2022. https://eprints.qut.edu.au/227734/1/Jessica_Alves_Thesis.pdf.

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Direct laser writing is a technique for printing complex 3D structures with high resolution by irradiating a photoresist in a two-photon process. Improved resolution and dynamic material properties of the printed structures is critical. Herein, advanced photochemical systems were investigated, potentially enabling dual-wavelength direct laser writing. Such systems consisting of organic photoswitches enable the formation of a single product only when irradiated with two wavelengths. A well-known class of photoswitches was investigated for this purpose and its chemistry was carefully explored. Further, photocatalysis combined with a photoswitch was identified as a possible strategy for the two-colour activated photoresist development.
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Bennes, Raphael Michel. "Recognition-induced control and acceleration of Diels-Alder cycloadditions." Thesis, University of Birmingham, 2000. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.368517.

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Wijnen, Jan Willem. "Cycloadditions in aqueous media." [S.l. : [Groningen] : s.n.] ; [University Library Groningen] [Host], 1997. http://irs.ub.rug.nl/ppn/159343356.

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Books on the topic "Diels-Alder cycloaddition reactions"

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Hamer, Jan. 1,4-Cycloaddition Reaction : the Diels-Alder Reaction in Heterocyclic Syntheses: The Diels-Alder Reaction in Heterocyclic Syntheses. Elsevier Science & Technology Books, 2013.

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Book chapters on the topic "Diels-Alder cycloaddition reactions"

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Kitamura, Chitoshi. "Synthesis of Substituted Oligoacenes via Diels-Alder Reactions and Substituent Effects on Molecular Structure, Packing Arrangement, and Solid-State Optical Properties." In Methods and Applications of Cycloaddition Reactions in Organic Syntheses, 407–28. Hoboken, New Jersey: John Wiley & Sons, Inc., 2014. http://dx.doi.org/10.1002/9781118778173.ch14.

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Wu, Haoxing, and Neal K. Devaraj. "Inverse Electron-Demand Diels–Alder Bioorthogonal Reactions." In Cycloadditions in Bioorthogonal Chemistry, 109–30. Cham: Springer International Publishing, 2015. http://dx.doi.org/10.1007/978-3-319-29686-9_6.

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Abe, M., and T. Yamamoto. "Diels–Alder Cycloaddition Reactions." In Monocyclic Arenes, Quasiarenes, and Annulenes, 1. Georg Thieme Verlag KG, 2010. http://dx.doi.org/10.1055/sos-sd-045-00599.

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Glass, R. S. "Diels–Alder Cycloaddition Reactions." In Three Carbon-Heteroatom Bonds: Amides and Derivatives; Peptides; Lactams, 1. Georg Thieme Verlag KG, 2005. http://dx.doi.org/10.1055/sos-sd-022-00170.

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"Intermolecular Diels-Alder Reactions." In Cycloaddition Reactions in Organic Synthesis, 91–139. Elsevier, 1990. http://dx.doi.org/10.1016/b978-0-08-034712-7.50007-2.

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"Intramolecular Diels-Alder Reactions." In Cycloaddition Reactions in Organic Synthesis, 140–208. Elsevier, 1990. http://dx.doi.org/10.1016/b978-0-08-034712-7.50008-4.

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Clayden, Jonathan, Nick Greeves, and Stuart Warren. "Pericyclic reactions 1: cycloadditions." In Organic Chemistry. Oxford University Press, 2012. http://dx.doi.org/10.1093/hesc/9780199270293.003.0034.

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This chapter describes pericyclic reactions. In pericyclic reactions, electrons move round a circle and there are no positive or negative charges on any intermediates, indeed, there are no intermediates at all. The most famous example is the Diels–Alder reaction, which goes in a single step simply on heating. The electrons do not really rotate at all; in reality, two π bonds disappear and two σ bonds take their place by the electrons moving smoothly out of the π orbitals into the σ orbitals. Such a reaction is called a cycloaddition. The chapter then looks at regioselectivity in Diels–Alder reactions, and other thermal and photochemical cycloadditions.
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Ian, Fleming. "Cycloaddition reactions." In Pericyclic Reactions. Oxford University Press, 2015. http://dx.doi.org/10.1093/hesc/9780199680900.003.0002.

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This chapter considers cycloadditions as the most useful of all pericyclic reactions in organic synthesis. It describes the wide range of known cycloadditions, identifies the conditions under which they take place, draws attention to their regio- and stereochemistry, and gives the simple rules for which of them take place and which do not. It also mentions the most important type of cycloaddition, the Diels–Alder reaction, which is essentially the reaction between butadiene and ethylene which form cyclohexene. The chapter talks about the carbonyl group, which is a substituent attached to the periphery that affects the rate but does not change the fundamental nature of the reaction. It refers to dipoles which react with alkenes or alkynes, or with heteroatom-containing double and triple bonds that form heterocyclic rings.
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"2. Diels–Alder cycloaddition reactions." In High Pressure Organic Synthesis, 23–76. Berlin, Boston: De Gruyter, 2019. http://dx.doi.org/10.1515/9783110556841-002.

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Procter, Garry. "Additions to C-C double bonds." In Asymmetric Synthesis, 101–47. Oxford University PressOxford, 1996. http://dx.doi.org/10.1093/oso/9780198557265.003.0006.

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Abstract Additions to C-C double bonds represent an important general area for asymmetric synthesis, not Jeast because several chiral centres can be established in a single reaction. One of the most thoroughly studied class of reactions of this type is the Diels-Alder reaction and related 4+2 cycloadditions. In its most general form the Diets-Alder reaction involves three important components, the dienophile, the diene, and the catalyst. The last is not always necessary, but it is often difficult to achieve high levels of stereoselectivity without the help of a Lewis acid catalyst. In addition to increasing the rate of reaction, the catalyst usually improves the regioselectivity and stereoselectivity of the cycloaddition. A detailed discussion of the mechanism of Diels-Alder reactions, and related theory, is not within the scope of this volume. Nevertheless. a much simplified brief outline follows, in order to aid understanding of the models that have been proposed to account for the stereochemical outcome of the reactions which will be discussed.
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Conference papers on the topic "Diels-Alder cycloaddition reactions"

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Kneeteman, María, Mauro Cainelli, Carla Ormachea, and Pedro Mancini. "THEORETICAL STUDY OF POTENTIALLY COMPLEX REACTIONS TO THE CYCLOADDITION PROCESS OF QUINOLINES IN HETERO DIELS-ALDER SYSTEMS." In The 19th International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2015. http://dx.doi.org/10.3390/ecsoc-19-e011.

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Doležal, Rafael, Natálie Karásková, Nadezhda V. Maltsevskaya, and Karel Kolář. "SUPPORTING CONCEPTUAL LEARNING IN ORGANIC CHEMISTRY THROUGH SEMI-EMPIRICAL MOLECULAR MODELING: HEURISTICS OF DIELS-ALDER [4+2] CYCLOADITIONS FOR PREPARATION OF POTENTIAL TLR4 MODULATORS." In Proceedings of the 2nd International Baltic Symposium on Science and Technology Education (BalticSTE2017). Scientia Socialis Ltd., 2017. http://dx.doi.org/10.33225/balticste/2017.39.

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A vast majority of novices in universities predominantly utilize algorithmic mental processes to resolve assigned tasks and tests. Although algorithmic thinking is an essential part of human cognitive functions, experts on didactics call for methods, which develop also conceptual thinking in beginners. Currently, heuristic molecular modeling gains an important position in chemistry education since it inherently integrates several conceptual thinking principles. Herein, it is focused on computational analysis of eight potential immunomodulators prepared by Diels-Alder reactions to exemplify conceptualized chemistry learning. Keywords: conceptual learning, diels-alder cycloadditions, molecular modeling, RM1, activation energy.
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