Relevant bibliographies by topics / Reverse Diels-Alder

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Academic literature on the topic 'Reverse Diels-Alder'

Author: Grafiati
Published: 5 June 2025
Last updated: 8 July 2025

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Journal articles on the topic "Reverse Diels-Alder"

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Zakharova, Daria V., Zalina A. Lok’yaeva, Alexander A. Pavlov, and Alexander V. Polezhaev. "New Chain Extenders for Self-Healing Polymers." Key Engineering Materials 899 (September 8, 2021): 628–37. http://dx.doi.org/10.4028/www.scientific.net/kem.899.628.

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We present here a small series of compounds designed to modify the polymer chain of various polyurethanes in order to introduce a structural fragment with the ability of thermally-triggered reversible covalent interactions. Bismaleimides (2a-2e) were synthesized from commercially available aromatic and aliphatic symmetric diamines (1a-1e) and were further introduced into the Diels-Alder reaction with furfuryl alcohol as dienophiles. The Diels-Alder adducts (3a-3e) were obtained as a mixture of endo- and exo-isomer. The presence of symmetrical hydroxyl groups in the structure of the obtained compounds makes them suitable as chain extenders of low molecular weight diisocyanate prepolymers. The presence of a thermally reversible Diels-Alder reaction adduct in the structure of potential chain-extenders opens a possibility to create unique materials with self-healing properties. All compounds obtained were characterized by 1H, 13C NMR, ESI-HRMS, and IR spectroscopy. The thermochemical parameters of the reverse Diels-Alder reaction were established using DSC analysis.
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Polezhaev, Alexander V., Daniel M. Beagan, Alyssa C. Cabelof, Chun-Hsing Chen, and Kenneth G. Caulton. "A substituent-tolerant synthetic approach to N/P-“loaded” heteroarenes." Dalton Transactions 47, no. 17 (2018): 5938–42. http://dx.doi.org/10.1039/c8dt00533h.

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Borisevich, Sophia S., Alena V. Kovalskaya, Inna P. Tsypysheva, and Sergey L. Khursan. "Thermodynamically controlled Diels–Alder reaction of 12-N-methylcytisine: A DFT study." Journal of Theoretical and Computational Chemistry 13, no. 06 (2014): 1450048. http://dx.doi.org/10.1142/s0219633614500485.

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A DFT study was performed for the Diels–Alder traction of 12-N-methylcytisine with a number of dienophiles (in boiling toluene under atmospheric pressure), namely, N-phenylmaleimide, maleic anhydride, 2,4-benzoquinone, tetracyanoethylene and methyl methacrylate. It was shown that 12-N-methylcytisine selectively reacts with these dienophiles, only the reaction with N-phenylmaleimide (NPM) resulting in the formation of thermodynamically stable adducts, which is consistent with experimental data. This selectivity of 12-N-methylcytisine is attributable to the difference between the properties of the listed dienophiles, which is confirmed by the relative reactivity indices calculated within the framework of the frontier molecular orbital (FMO) and hard and soft (Lewis) acids and bases (HSAB) theories, the thermodynamic and activation parameters of the forward and retro-Diels–Alder reactions. According to analysis of the theoretical results, NPM is characterized by high chemical potential, hardness close to that of 12-N-methylcytisine, and commensurable heights of the activation barriers for the forward and reverse Diels–Alder reactions and also forms stable [4+2] adducts.
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Buttery, JH, J. Moursounidis, and D. Wege. "A,B-Diheteropentalenes by a Tandem Intramolecular Diels-Alder/Reverse Diels-Alder Reaction Sequence. Application to the Synthesis of Thieno[3,4-b]furan." Australian Journal of Chemistry 48, no. 3 (1995): 593. http://dx.doi.org/10.1071/ch9950593.

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Alkylation of 2-furylmethanethiol (28) with propargyl chloride gave the thioether (22) which on methoxycarbonylation afforded the acetylenic ester (30). On heating, this material underwent an intramolecular Diels -Alder reaction to give the tricyclic compound (32). In the presence of 3,6- di (pyridin-2′-yl)-s- tetrazine , (32) afforded methyl 4,6-dihydrothieno[3,4-b]furan-3-carboxylate (38) by a sequence involving a further Diels -Alder reaction followed by two reverse Diels-Alder reactions. The ester (38) could be dehydrogenated to give methyl thieno [3,4-b]furan-3-carboxylate (40) while hydrolysis of (38), followed by decarboxylation and dehydrogenation delivered the parent thieno [3,4-b]furan (5). 3-Methyl-4,6-dihydrothieno[3,4-b]furan (46) and 3-methylthieno[3,4-b]furan (47) were prepared; a comparison of the 4JMe-C=C-H coupling constants in the 1H n.m.r . spectra of (46) and (47) suggests that an increase in the C2-C3 furyl bond order accompanies the (46) → (47) conversion. Methyl 4,6-dihydrofuro[3,4-b]furan-3-carboxylate (39), 4,6-dihydrofuro[3,4-b]furan (27) and methyl 4,6-dihydro-6-phenylfuro[3,4-b]furan-3-carboxylate (53) were prepared by an analogous tandem reaction sequence. These compounds could not be dehydrogenated to the fully conjugated furo [3,4-b]furan ring system.
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Bertholio, Frédéric, Pierre Mison, Thierry Pascal, and Bernard Sillion. "Mechanism of endo-exo isomerization of nadimide end-capped oligomers." High Performance Polymers 5, no. 1 (1993): 47–57. http://dx.doi.org/10.1088/0954-0083/5/1/005.

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Before polymerization, nadimide end-capped polyimide oligomers exist in the endo form. During the cure, an endo-exo equilibrium takes place. This paper discusses the relationship between endo-exo isomerization and the reverse-Diels-Alder reaction of the nadinaide system. As a consequence of the experimental results, an explanation for cyclopentadiene evolution during the polymerization of nadimide systems is given.
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Garcia, J. Gabriel, Frank R. Fronczek, and Mark L. McLaughlin. "Tandem reverse-electron-demand diels-alder reactions of 1,5-cyclooctadiene." Tetrahedron Letters 32, no. 28 (1991): 3289–92. http://dx.doi.org/10.1016/s0040-4039(00)92688-1.

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Harriman, D. Joseph, and Ghislain Deslongchamps. "Reverse-docking study of the TADDOL-catalyzed asymmetric hetero-Diels–Alder reaction." Journal of Molecular Modeling 12, no. 6 (2006): 793–97. http://dx.doi.org/10.1007/s00894-006-0097-z.

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GARCIA, J. G., F. R. FRONCZEK, and M. L. MCLAUGHLIN. "ChemInform Abstract: Tandem Reverse-Electron-Demand Diels-Alder Reactions of 1,5- Cyclooctadiene." ChemInform 23, no. 15 (2010): no. http://dx.doi.org/10.1002/chin.199215069.

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Tsai, Tzeng-Guang, and Chin-Hui Yu. "Effect of Orbital Overlap in Thermal Reverse Homo-Diels-Alder Reaction and Intramolecular Reverse Ene Reaction." Journal of the Chinese Chemical Society 41, no. 6 (1994): 631–34. http://dx.doi.org/10.1002/jccs.199400088.

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Zhang, Jianyuan, Yanbang Li, Yue Sun, and William Kopcha. "(Invited) Multicomponent Reactions Towards New Fullerene and Metallofullerene Derivatives." ECS Meeting Abstracts MA2022-01, no. 11 (2022): 813. http://dx.doi.org/10.1149/ma2022-0111813mtgabs.

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Fullerenes and endohedral metallofullerenes (EMFs) are molecular building blocks for a variety of organic materials widely applicable in photovoltaics, catalysis, quantum information science, semi-conductors, biomedicines, and so on. Regioselective functionalization reactions are essential for the construction of fullerene and EMF materials. Multicomponent reactions that generate reactive species to be captured by the double bonds on fullerenes or EMFs represent a useful approach to develop new reactions. In this presentation we hope to share our recent work in the development of new reactions for fullerene and EMF functionalizations, including isocyanide-induced reactions, reverse electron demand Diels-Alder reactions, and aminations.
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Dissertations / Theses on the topic "Reverse Diels-Alder"

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Aumand, Livia M. "A Studies towards the formation of asymmetric quaternary centres via radical allylation B Applications of chiral hydrazide organocatalysts to Diels-Alder, hydride reduction, and alpha-chlorination reactions C Studies directed towards the synthesis of potential HIV-1 reverse transcriptase inhibitors: 9-Alkylaryl TIBO derivatives." Thesis, University of Ottawa (Canada), 2005. http://hdl.handle.net/10393/26843.

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In part A, the attempts at synthesizing quaternary centres via radical reactions are described. Using tartrate acetals as chiral auxiliaries, tertiary bromides were submitted to radical allylation conditions in an effort to form 1,3-dicarbonyl compounds 27 possessing an asymmetric quaternary centre at C2.* Part B describes the synthesis of chiral hydrazide 129 and its ability to catalyze the Diels-Alder reaction is examined. The application of chiral hydrazides 131 to the organocatalytic hydride reduction of alpha,beta-unsaturated aldehydes and the alpha-chlorination of aldehydes is also recounted herein.* Finally, in Part C, efforts towards the synthesis of potential broad spectrum HIV-1 reverse transcriptase inhibitors are described. Compounds 161 are based on the TIBO family of compounds and possess a novel alkylaryl appendage.* *Please refer to dissertation for diagrams.
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Book chapters on the topic "Reverse Diels-Alder"

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Dutruch, L., M. Senneron, M. Bartholin, P. Mison, and B. Sillion. "Preparation of Thermostable Rigid Foams by Control of the Reverse Diels—Alder Reaction During the Cross-Linking of Bis-nadimide Oligomers." In ACS Symposium Series. American Chemical Society, 1997. http://dx.doi.org/10.1021/bk-1997-0669.ch004.

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Dzierba, C. D., K. S. Zandi, T. Mollers, and K. J. She.a,. "The Total Synthesis of (+)-Adrenosterone." In Exercises in Synthetic Organic Chemistry. Oxford University PressOxford, 1997. http://dx.doi.org/10.1093/oso/9780198559443.003.0058.

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Abstract Discussion Points When ethylene glycol was used instead of (-)-hydroxybenzoin (step e) in the preparation of the silicon tether, the intramolecular Diels-Alder reaction of step h proceeded with reverse diastereoselectivity, affording a mixture corresponding to 6:7 in a 1:10 ratio. Give an explanation for this finding. Further Reading For a review on silicon-tethered reactions, see: M. Bois and T. Skrydstrup, Chem. Rev.,1995, 95,1253.
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Taber, Douglass F. "Tethered Diels-Alder Cycloaddition: (±)-Neovibsanin B (Imagawa, Nishizawa), Valerenic Acid (Mulzer), (-)-Himandrine (Movassaghi), (±)-Pallavicinolide A (Wong), (+)-Phomopsidin (Nakada)." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0077.

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It has generally been observed that prospective intramolecular Diels-Alder cycloadditions that would form a γ-lactone are reluctant to proceed. In the course of a synthesis of (±)-neovibsanin B 4, Hiroshi Imagawa and Mugio Nishizawa of Tokushima Bunri University reversed (Organic Lett. 2009, 11, 1253) the usual connectivity and found that the dienyl ester 1 could be induced to cyclize to 3. The solvent 2 improved both the yield and the diastereoselectivity of the cycloaddition. It was not surprising that Johann Mulzer of the University of Vienna could see (Organic Lett. 2009, 11, 1151) no evidence of cyclization on heating the acrylate 5. In contrast, following the lead of Barriault, they found that MgBr2 -tethered cycloaddition of methyl acrylate 7 with the alcohol 6 proceeded smoothly, to give 8, which they carried on to valerenic acid 9. Intramolecular Diels-Alder reactions to form 6,6-systems are often facile. Mohammad Movassaghi of MIT, en route to (-)-himandrine 12, showed (J. Am. Chem. Soc. 2009, 131, 9648) that the tetraene 10 cyclized to 11 at 95°C with 5:1 dr. In this case the solvent was the more typical acetonitrile with 10% diethyl aniline. The intramolecular Diels-Alder reaction is concerted but nonsynchronous (Tetrahedron Lett. 1981, 22, 5141), with β-bond formation preceding α-bond formation. This contributes to the reluctance of 8 to cyclize. In contrast, Henry N. C. Wong of the Chinese University of Hong Kong observed (Angewandte Chem. Int. Ed. 2009, 48, 2351) that the tetraene 13, which is polarity matched, cyclized to 14 spontaneously as soon as it was formed. Functional group conversion completed the synthesis of (±)-pallavicinolide A 15. The transannular Diels-Alder (TADA) reaction can proceed with high diastereocontrol, but the factors directing these cyclizations are not completely understood. In the course of a synthesis of (+)-phomopsidin 18, Masahisa Nakada of Waseda University found (Tetrahedron 2009, 65, 888) that 16 led to 17 with 16:1 dr. In contrast, the triene epimeric to 16 at the silyloxy group cyclized with only 2:1 dr.
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Taber, Douglass F. "Intramolecular Diels-Alder Cycloaddition: 7-Isocyanoamphilecta- 11(20),15-diene (Miyaoka), (–)-Scabronine G (Kanoh), Basiliolide B (Stoltz), Hirsutellone B (Uchiro), Echinopine A (Chen)." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0078.

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The amphilectane diterpenes, exemplified by 7-isocyanoamphilecta-11(20),15-diene 3, have been little investigated. In the course of a synthesis of 3, Hiroaki Miyaoka of the Tokyo University of Pharmacy and Life Sciences took advantage (Synlett 2011, 547) of the kinetic enolization and silylation of 1 to convert it into a trienone that spontaneously cyclized to 2. Scabronine G 6, isolated from the mushroom Sarcodon scabrosus, was found to enhance the secretion of neurotrophic factors from 1321N1 astrocytoma cells. To set the absolute configuration of the two quaternary centers that are 1, 4 on the cyclohexane ring of 6, Naoki Kanoh and Yoshiharu Iwabuchi of Tohoku University cyclized (Org. Lett. 2011, 13, 2864) 4 to 5. Although described by the authors as a double Michael addition, this transformation has the same connectivity as an intramolecular Diels-Alder cycloaddition. The diterpenes isolated from the genus Thapsia, represented by basiliolide B 9, induce rapid mobilization of intracellular Ca2+ stores. Brian M. Stoltz of Caltech effected (Angew. Chem. Int. Ed. 2011, 50, 3688) Claisen rearrangement of 7 to give an intermediate that cyclized to 8 as a mixture of diastereomers. A significant challenge in the synthesis was the assembly of the delicate enol ether/lactone of 9. Hirsutellone B 12, isolated from Hirsutella nivea, shows significant antituberculosis activity. Hiromi Uchiro of the Tokyo University of Science found it useful (Org. Lett. 2011, 13, 6268) to protect the intermediate unsaturated keto ester by intermolecular cycloaddition with pentamethylcyclopentadiene before constructing the triene of 10. Simple thermolysis reversed the intermolecular addition, opening the way to intramolecular cycloaddition to give 11. The tetracyclic ring system of the diterpene echinopine A 15 represents a substantial synthetic challenge. David Y.-K. Chen of Seoul National University approached this problem (Org. Lett. 2011, 13, 5724) by Pd-mediated cyclization of 13 to the diene, which then underwent intramolecular Diels-Alder cycloaddition to give 14, with control of the relative configuration of two of the three ternary centers of 15. Double bond migration followed by oxidative cleavage of the resulting cyclohexenone then set the stage for the intramolecular cyclopropanation that completed the synthesis of 15.
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Taber, Douglass F. "Alkene and Alkyne Metathesis: Grandisol (Goess), 8-Epihalosilane (Kouklovsky/Vincent), (+)-Chinensiolide B (Hall)." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0033.

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The cost of using Grubbs-type catalysts could be reduced dramatically if the turnover could be improved. Richard L. Pederson of Materia found (Organic Lett. 2010, 12, 984) that in MTBE at 50°C, the ring-closing metathesis of 1 proceeded to completion in 8 hours with just 500 ppm of H2 catalyst 2. Jianhui Wang of Tianjin University constructed (Angew. Chem. Int. Ed. 2010, 49, 4425) a modified H2 catalyst 5 tethered to a nitrobenzospiropyran. After the cyclization of 4 to 6 was run in CH2Cl2, the mixture was irradiated with visible light, converting 5 into its ionic form, which could be extracted with glycol/methanol, leaving little Ru residue in the cyclized product. In the dark, the catalyst reverted and could be extracted back into CH2Cl2 and reused. In a complementary approach, David W. Knight of Cardiff University found (Tetrahedron Lett. 2010, 51, 638) that the residual Ru after metathesis could be reduced to < 2 ppm simply by stirring the product with H2O2. Cyclopropenes such as 6 are readily available in enantiomerically pure form by the addition of diazoacetates to alkynes. Christophe Meyer and Janine Cossy of ESPCI ParisTech showed (Organic Lett. 2010, 12, 248) that with a Ti additive, G2 cyclized 7 to 8. Siegfried Blechert of the Technische Universität Berlin devised (Angew. Chem. Int. Ed. 2010, 49, 3972) the chiral Ru catalyst 11, which converted the prochiral 9 to 12 in high ee. Daesung Lee of the University of Illinois, Chicago, explored (J. Am. Chem. Soc. 2010, 132, 8840) the cyclization of the diyne 13 with 14 under G2 catalysis. Depending on the terminal substituent, the cyclization could be directed selectively to 15 or 16. Bran C. Goess of Furman University took advantage (J. Org. Chem. 2010, 75, 226) of alkyne ring-closing metathesis for the conversion of 17 to 18. Selective hydrogenation then delivered the boll weevil pheromone grandisol 19. Cyrille Kouklovsky and Guillaume Vincent of the Université de Paris Sud extended (J. Org. Chem. 2010, 75, 4333) ring-opening/ring-closing metathesis to the nitroso Diels-Alder adduct 20. Reduction led to 8-epihalosilane 22.
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