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Journal articles on the topic 'Diels Alder addition'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Hopf, Henning, and Marcus Theurig. "Synthesis of Enediynes by Diels-Alder Addition." Angewandte Chemie International Edition in English 33, no. 10 (1994): 1099–100. http://dx.doi.org/10.1002/anie.199410991.

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2

Hopf, Henning, and Marcus Theurig. "Synthese von Endiinen durch Diels-Alder-Addition." Angewandte Chemie 106, no. 10 (1994): 1173–74. http://dx.doi.org/10.1002/ange.19941061025.

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3

Teixeira, Filipe, André Melo, and M. Natália D. S. Cordeiro. "Aza-Diels–Alder addition of cyclopentadiene to propynyliminoglyoxylates." Computational and Theoretical Chemistry 1012 (May 2013): 54–59. http://dx.doi.org/10.1016/j.comptc.2013.02.014.

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4

Hamrock, Steven J., and Robert S. Sheridan. "Photochemical Diels-Alder addition of N-methyltriazolinedione to phenanthrene." Tetrahedron Letters 29, no. 43 (1988): 5509–12. http://dx.doi.org/10.1016/s0040-4039(00)80799-6.

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5

Donegan, Gregory, Ronald Grigg, Frances Heaney, Sivagnanasundram Surendrakumar, and William J. Warnock. "Consecutive diels-alder- michael addition - 1,3-dipolar cycloaddition processes." Tetrahedron Letters 30, no. 5 (1989): 609–12. http://dx.doi.org/10.1016/s0040-4039(00)95268-7.

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6

Zhang, Lei, Jianzhong Yang, Christopher L. Edwards, Lawrence B. Alemany, Valery N. Khabashesku, and Andrew R. Barron. "Diels–Alder addition to fluorinated single walled carbon nanotubes." Chemical Communications, no. 26 (2005): 3265. http://dx.doi.org/10.1039/b500125k.

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7

Brimble, Margaret A., John F. McEwan, and Peter Turner. "Asymmetric Diels–Alder addition of cyclopentadiene to chiral naphthoquinones." Tetrahedron: Asymmetry 9, no. 7 (1998): 1239–55. http://dx.doi.org/10.1016/s0957-4166(98)00087-1.

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8

Döpp, Dietrich, and Michael Pies. "High asymmetic induction in a photo-Diels–Alder addition." J. Chem. Soc., Chem. Commun., no. 22 (1987): 1734–35. http://dx.doi.org/10.1039/c39870001734.

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9

Miller, Bernard, and Dumitru Ionescu. "An addition—cyclization—elimination mechanism for dehydro Diels-Alder reactions." Tetrahedron Letters 35, no. 36 (1994): 6615–18. http://dx.doi.org/10.1016/s0040-4039(00)73449-6.

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10

ZHANG, X., Q. JIANG, Z. XIONG, J. ZOU, L. WANG, and Z. MI. "Diels-Alder Addition of Dicyclopentadiene with Cyclopentadiene in Polar Solvents." Chemical Research in Chinese Universities 24, no. 2 (2008): 175–79. http://dx.doi.org/10.1016/s1005-9040(08)60036-7.

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11

Meador, Mary Ann B., Michael A. Meador, Myong Ku Ahn, and Michael A. Olshavsky. "Evidence for thermal dehydration occurring in Diels-Alder addition polymers." Macromolecules 22, no. 11 (1989): 4385–87. http://dx.doi.org/10.1021/ma00201a039.

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12

Fernandes, F. M., R. Araújo, M. F. Proença, C. J. R. Silva, and M. C. Paiva. "Functionalization of Carbon Nanofibers by a Diels-Alder Addition Reaction." Journal of Nanoscience and Nanotechnology 7, no. 10 (2007): 3514–18. http://dx.doi.org/10.1166/jnn.2007.818.

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13

Liu, Hsing-Jang, Dan-Xiong Wang, Jeung Bea Kim, Eric N. C. Browne, and Yu Wang. "Activated cyclooctenones are effective dienophiles." Canadian Journal of Chemistry 75, no. 6 (1997): 899–912. http://dx.doi.org/10.1139/v97-108.

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The first Diels–Alder addition of a diene to a cyclooctenone dienophile has been observed. Three activated cyclooctenone dienophiles 1, 2, and 3 are studied with a variety of simple and functionalized dienes. Diels–Alder adducts are produced in excellent yields under very mild Lewis acid catalyzed conditions. The usual orientation rules are followed and, as predicted, the products are formed for the most part exclusively by ester-endo addition. The stereoselectivity is influenced by the substitution pattern of the diene in some cases. The factors influencing the stereochemical selectivity of t

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14

Liu, Hsing-Jang, Wen-Lung Yeh, and Eric N. C. Browne. "Activated cycloheptenone dienophiles. A versatile approach to 6,7-fused ring targets." Canadian Journal of Chemistry 73, no. 7 (1995): 1135–47. http://dx.doi.org/10.1139/v95-140.

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Several 2-carbalkoxy-2-cyclohepten-1-ones were prepared and their Diels–Alder characteristics examined in order to develop a facile general approach to the synthesis of cycloheptane ring-containing polycyclic natural products. Substitution pattern on the seven-membered ring was found to greatly affect the Diels–Alder behavior. In addition, some extraordinary facial stereoselectivity was observed. Keywords: Diels–Alder reaction, 2-carbalkoxy-2-cyclohepten-1-ones, 6,7-fused ring system.

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15

Calhoun, Glenn C., and Gary B. Schuster. "Triplex catalyzed diels-alder reactions: Addition of indene to 1,3-cyclohexadiene." Tetrahedron Letters 27, no. 8 (1986): 911–14. http://dx.doi.org/10.1016/s0040-4039(00)84135-0.

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16

Garvin, Gregory G., Timothy J. Sloan, and Richard J. Puddephatt. "The dimerization of diphenyl(cyclopentadienyl)phosphine ligands by Diels-Alder addition." Polyhedron 6, no. 9 (1987): 1797–802. http://dx.doi.org/10.1016/s0277-5387(00)86553-5.

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17

Yilmaz, Özgür, Nermin Simsek Kus, Tuncay Tunç, and Ertan Sahin. "Diels–Alder reactions: The effects of catalyst on the addition reaction." Journal of Molecular Structure 1098 (October 2015): 72–75. http://dx.doi.org/10.1016/j.molstruc.2015.06.012.

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18

Brimble, Margaret A., Richard J. Elliott, and John F. McEwan. "ChemInform Abstract: Diels-Alder Addition of Acyclic Dienes to Chiral Naphthoquinones." ChemInform 32, no. 12 (2001): no. http://dx.doi.org/10.1002/chin.200112109.

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19

BRIMBLE, M. A., J. F. MCEWAN, and P. TURNER. "ChemInform Abstract: Asymmetric Diels-Alder Addition of Cyclopentadiene to Chiral Naphthoquinones." ChemInform 29, no. 34 (2010): no. http://dx.doi.org/10.1002/chin.199834042.

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20

Lanzendörfer, Franz, and Manfred Christl. "3,4-Bismethylentricyclo[3.1.0.0]hexan - Synthese und Diels-Alder-Addition an Tetracyanethylen." Angewandte Chemie 95, no. 11 (2006): 896–97. http://dx.doi.org/10.1002/ange.19830951112.

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21

Reveles, J. Ulises, Govinda KC, Tunna Baruah, and Rajendra R. Zope. "Diels-Alder addition to H2O@C60 an electronic and structural study." Chemical Physics Letters 685 (October 2017): 198–204. http://dx.doi.org/10.1016/j.cplett.2017.07.062.

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22

Rozek, Tomas, Tomas Rozek, Dennis K. Taylor, et al. "Syntheses of Angucyclinones Related to Ochromycinone. III. An 11-Hydroxy Isomer and Some Reduced Analogues." Australian Journal of Chemistry 52, no. 2 (1999): 129. http://dx.doi.org/10.1071/c98124.

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The boron triacetate assisted Diels Alder reaction between racemic 5,5-dimethyl-3-vinylcyclohex- 2-enyl acetate and 5-hydroxynaphthoquinone yields the racemic 11-hydroxy-3,3-dimethyl-7,12-dioxo- 1,2,3,4,6,6a,7,12,12a,12b-decahydrobenzo[a]anthracen-1-yl acetate as the sole stereoisomer by regio- and stereo-selective cis endo addition. Aromatization of the Diels Alder adduct followed by hydrolysis of the acetate and oxidation of the resultant 1-hydroxy group gives the target angucyclinone, 11-hydroxy-3,3-dimethyl-1,2,3,4,7,12-hexahydrobenzo[a]anthracene-1,7,12-trione, in an overall yield of 37%

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23

Constantino, Mauricio, Valdemar Júnior, and Gil Da Silva. "Niobium Pentachloride Activation of Enone Derivatives: Diels-Alder and Conjugate Addition Products." Molecules 7, no. 5 (2002): 456–64. http://dx.doi.org/10.3390/70500456.

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24

Demircan, Aydin. "Radical Addition to Substituted Furans: Diels-Alder Like Products Versus Fragmentation Reactions." Synlett 1998, no. 11 (1998): 1215–16. http://dx.doi.org/10.1055/s-1998-1916.

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25

Hartsough, David, and Gary B. Schuster. "The triplex Diels-Alder reaction: stereospecific addition of methylstyrenes to 1,3-cyclohexadiene." Journal of Organic Chemistry 54, no. 1 (1989): 3–4. http://dx.doi.org/10.1021/jo00262a001.

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26

Mach, Karel, Helena Antropiusová, Vladimír Hanuš, and Petr Sedmera. "Titanium-catalyzed Diels-Alder addition of bis(trimethylsilyl)acetylene to 1,3-cyclohexadiene." Collection of Czechoslovak Chemical Communications 54, no. 11 (1989): 3088–91. http://dx.doi.org/10.1135/cccc19893088.

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The TiCl4-(C2H5)2AlCl catalyst induced the Diels-Alder addition of bis(trimethylsilyl)acetylene to 1,3-cyclohexadiene affording 2,3-bis(trimethylsilyl)bicyclo[2.2.2]octa-2,5-diene in 72% yield under mild conditions. The product eliminates ethylene upon heating to 240 °C to give 1,2-bis(trimethylsilyl)benzene.

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27

Bah, Juho, and Johan Franzén. "Carbocations as Lewis Acid Catalysts in Diels-Alder and Michael Addition Reactions." Chemistry - A European Journal 20, no. 4 (2013): 1066–72. http://dx.doi.org/10.1002/chem.201304160.

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28

MILLER, B., and D. IONESCU. "ChemInform Abstract: An Addition-Cyclization-Elimination Mechanism for Dehydro Diels-Alder Reactions." ChemInform 26, no. 5 (2010): no. http://dx.doi.org/10.1002/chin.199505068.

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29

Liu, Xu, Fangbo Liu, Simeng Liu, Min Cui, and Jianru Deng. "Relationship on structure and properties of polyurethane modified Diels-Alder addition polymer." Journal of Applied Polymer Science 136, no. 15 (2018): 47355. http://dx.doi.org/10.1002/app.47355.

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30

Salaheddine, Hegazi, Soumia Lafquih Titouani, Mohamed Soufiaoui, and Abderrahim Tahdi. "ChemInform Abstract: Hetero-Diels-Alder Reactions: Addition of Azostyrenes to 2-Hydroxymethyleneindanones." ChemInform 33, no. 38 (2010): no. http://dx.doi.org/10.1002/chin.200238089.

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31

Gandhi, R. P., M. P. S. Ishar, and A. Wali. "Diels–Alder addition of cyclopentadiene to allenic esters: catalysis by lanthanide complexes." J. Chem. Soc., Chem. Commun., no. 16 (1988): 1074–75. http://dx.doi.org/10.1039/c39880001074.

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32

Kawakami, Hiroki, Hiroshi Okada, and Yutaka Matsuo. "Efficient Diels–Alder Addition of Cyclopentadiene to Lithium Ion Encapsulated [60]Fullerene." Organic Letters 15, no. 17 (2013): 4466–69. http://dx.doi.org/10.1021/ol4020046.

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33

Pla, Paula, Yang Wang, and Manuel Alcamí. "Simple bond patterns predict the stability of Diels–Alder adducts of empty fullerenes." Chemical Communications 54, no. 33 (2018): 4156–59. http://dx.doi.org/10.1039/c8cc01709c.

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A systematic study of Diels–Alder cycloadditions to empty fullerenes reveals that π effects control site preference. Simple Hückel calculation allows to obtain quantitative descriptors and to understand why addition occurs preferentially at certain types of bonds. A couple of simple rules are proposed as a visual guide for a rapid prediction of Diels–Alder reactivity.

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34

Čermák, Jan, Magdalena Kvíčalová, Jan Schraml, and Martin Čapka. "Diels-Alder Self-Addition and Retroaddition of (Cyclopentadienylmethyl)triethoxysilane and Synthesis of its Permethylated Analogue." Collection of Czechoslovak Chemical Communications 59, no. 2 (1994): 453–56. http://dx.doi.org/10.1135/cccc19940453.

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Reversible Diels-Alder self-addition of (cyclopentadienylmethyl)triethoxysilane hampering its use as functionalizing agent and the synthesis of a new silica functionalizing agent, (tetramethylcyclopentadienylmethyl)triethoxysilane, are described.

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35

Itoh, Kuniaki, Kazue Kitoh, and Shigehisa Kishimoto. "Concerted and stepwise mechanisms in the DielsAlder and Michael reactions of furans with methyl 3-nitroacrylate Experimental and theoretical studies." Canadian Journal of Chemistry 84, no. 3 (2006): 392–406. http://dx.doi.org/10.1139/v06-013.

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The DielsAlder reactions of the furans (1a1c) and methyl 3-nitroacrylate (2) produce the cycloadducts via a concerted mechanism. Then, the products subsequently undergo retro-DielsAlder reactions to give the Michael adducts via a stepwise mechanism. We have used both experimental and theoretical methods to investigate the mechanism for, and the regio- and stereo-selectivity in, the DielsAlder and Michael reactions. To account for the selectivity observed in these additions, we examined the frontier molecular orbitals involved, and to locate the transition states (TS), we employed a B3LYP/6

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36

Leigh, William J., Donald W. Hughes, and D. Scott Mitchell. "Competitive Diels–Alder and ene addition of N-arylmaleimides to 7-dehydrocholesteryl acetate." Canadian Journal of Chemistry 70, no. 11 (1992): 2730–44. http://dx.doi.org/10.1139/v92-347.

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Thermolysis of N-phenyl, N-para-biphenyl, and N-para, para′-terphenylmaleimide with 7-dehydrocholesteryl acetate in benzene solution at 200 °C yields mixtures of four cycloadducts in relative yields that are essentially independent of the maleimide substituent. The three major products are those of ene addition to C7 of the steroid with abstraction of the proton at C9 or C14. The α-endo-Diels-Alder adduct is formed as a minor product. The structures of the adducts have been elucidated on the basis of one- and two-dimensional 1H and 13C NMR spectroscopic techniques, including homonuclear 1H dec

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37

Dao, B., J. H. Hodgkin, and T. C. Morton. "The Utility of 2-Naphthol Derivatives As Diels–Alder Based Co-Reactants for Bismaleimides." High Performance Polymers 9, no. 4 (1997): 413–27. http://dx.doi.org/10.1088/0954-0083/9/4/005.

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A number of 2-naphthols were found to undergo a Diels–Alder addition reaction with maleimides. This reaction can be used to bring about the cure of bismaleimides. The simplest co-reactant prepared in this work was 7-allyloxy-2-naphthol and satisfactory cures were obtained with appropriate bismaleimides. However, the laminate coupons made using this system had lower thermal stability than those of a comparable system using the commercial co-reactant Matrimid 5292B. The performance of this new chemistry was further tested by incorporating the naphthol/maleimide Diels–Alder addition structure int

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38

Cameron, DW, RW Read, and J. Stavrakis. "Reactions of Dimethyl (2'-Oxopropylidene)Propanedioate and Dimethyl (3'-Bromo-2'-oxopropylidene)propanedioate, Two Highly Electrophilic Trisubstituted Alkenes." Australian Journal of Chemistry 40, no. 11 (1987): 1831. http://dx.doi.org/10.1071/ch9871831.

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The keto diester, dimethyl (2'-oxopropylidene)propanedioate, and its new 3'-bromo derivative have been made to react with a variety of nucleophilic reagents. Low molecular weight products have been obtained efficiently by processes involving conjugate addition, Diels-Alder reaction, Diels-Alder reaction having inverse electron demand, or ene reaction. Regiochemistry of the reactions is controlled by the dominant withdrawing effect of the two geminal ester groups. The amine addition products of the bromo keto diester were found to undergo a novel secondary dehydrobromination reaction under alka

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39

Jankowski, Christopher K., André Pelletier, Eduardo Diaz T., et al. "On the origin of some cubebene derivatives — Diels–Alder adducts and the diene structures of solidago compounds." Canadian Journal of Chemistry 85, no. 11 (2007): 996–1005. http://dx.doi.org/10.1139/v07-112.

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Two reactions, HCl addition and the thermal and (or) microwave assisted Diels–Alder condensation, were performed on α-cubebene (1), a vinylcyclopropane-containing tricyclic sesquiterpene. The diene structures originating from these reactions and from subsequent rearrangements of 1 were identified. The stereochemistry of the resulting adducts was established using mostly 2D high-resolution NMR.Key words: cubebene, tricyclic terpenes from Solidago Canadensis L, Diels-Alder microwave condensation on vinylcyclopropane system.

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40

Downey, C. Wade, Smaranda Craciun, Christina A. Vivelo, Ana M. Neferu, Carly J. Mueller, and Stephanie Corsi. "One-pot three-step thioconjugate addition-oxidation-Diels–Alder reactions of ethyl propiolate." Tetrahedron Letters 53, no. 43 (2012): 5766–68. http://dx.doi.org/10.1016/j.tetlet.2012.08.054.

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41

Somei, Masanori, Yoshikazu Fukui, and Masakazu Hasegawa. "Preparations of Tryptamine-4,5-dinones, and Their Diels-Alder and Nucleophilic Addition Reactions." HETEROCYCLES 41, no. 10 (1995): 2157. http://dx.doi.org/10.3987/com-95-7189.

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42

Wang, Guan-Wu, Martin Saunders, and R. James Cross. "Reversible Diels−Alder Addition to Fullerenes: A Study of Equilibria Using3He NMR Spectroscopy." Journal of the American Chemical Society 123, no. 2 (2001): 256–59. http://dx.doi.org/10.1021/ja001346c.

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43

Salaheddine, Hegazi, Soumia Lafquih Titouani, Mohamed Soufiaoui, and Abderrahim Tahdi. "Réaction hétéro-Diels–Alder: addition des azostyrènes sur les dérivés 2-hydroxyméthylène indanones." Tetrahedron Letters 43, no. 24 (2002): 4351–53. http://dx.doi.org/10.1016/s0040-4039(02)00768-2.

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44

Eugui, Macarena, Katerine Rasquin, Andrés López Radcenco, Leopoldo Suescun, and Guillermo Moyna. "A Diels-Alder reaction / oxa-Michael addition / acyloin rearrangement cascade on tropolonic substrates." Tetrahedron Letters 59, no. 16 (2018): 1560–63. http://dx.doi.org/10.1016/j.tetlet.2018.03.022.

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45

Cabral, Jose, and Pierre Laszlo. "Product distribution in diels-alder addition of n-benzylidene aniline and enol ethers." Tetrahedron Letters 30, no. 51 (1989): 7237–38. http://dx.doi.org/10.1016/s0040-4039(01)93946-2.

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46

Frias, Célia F., Ana C. Fonseca, Jorge F. J. Coelho, and Arménio C. Serra. "Straightforward functionalization of acrylated soybean oil by Michael-addition and Diels–Alder reactions." Industrial Crops and Products 64 (February 2015): 33–38. http://dx.doi.org/10.1016/j.indcrop.2014.10.050.

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47

Cáceres-Castillo, David, Fernando Moguel-Pardío, Ramiro F. Quijano-Quiñones, Gumersindo Mirón-López, and Gonzalo J. Mena-Rejón. "Formation of Quercetin Heterodimer via Diels-Alder Type Cyclo-Addition under Microwave Conditions." Letters in Organic Chemistry 13, no. 2 (2016): 107–12. http://dx.doi.org/10.2174/1570178612666151008014708.

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48

Cabrera, Silvia, Olga García Mancheño, Ramón Gómez Arrayás, Inés Alonso, Pablo Mauleón, and Juan C. Carretero. "Sulfenylphosphinoferrocenes: Novel planar chiral ligands in enantioselective catalysis." Pure and Applied Chemistry 78, no. 2 (2006): 257–65. http://dx.doi.org/10.1351/pac200678020257.

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Structurally well-defined transition-metal complexes of 1-phosphino-2-sulfenylferrocene (Fesulphos ligands) act as highly efficient catalysts in a variety of mechanistically different transformations. Excellent enantioselectivities were achieved in Pd-catalyzed allylic substitutions, desymmetrization of meso-heterobicyclic alkenes by Pd-catalyzed addition of dialkylzinc reagents, Pd-catalyzed Diels-Alder reaction of cyclopentadiene with N-acryloyl oxazolidinones, and in Cu-catalyzed formal aza-Diels-Alder reaction of Danishefsky diene to N-sulfonyl aldimines.

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49

Tjepkema, Michael W., Peter D. Wilson, Hélène Audrain, and Alex G. Fallis. "Ring A building blocks for taxoids and taxamycins." Canadian Journal of Chemistry 75, no. 9 (1997): 1215–24. http://dx.doi.org/10.1139/v97-146.

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The syntheses of a series of oxygenated cyclohexene ring A synthohs 20, 22–27, 34, 36, and 37 that possess suitable functionality for further elaboration for taxoid synthesis are described. These compounds have been prepared from β-ionone by a series of oxidative and addition reactions or alternatively by Lewis acid catalyzed Diels–Alder cycloadditions with the oxygen-containing trimethyl substituted dienes 31 and 33. Keywords: taxoid, paclitaxel, dienes, Diels–Alder, β-ionone.

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50

Zhang, Min, and Guangchao Liang. "Understanding the sigmatropic shifts of cyclopenta-2,4-dien-1-yltrimethylsilane in its Diels–Alder addition." Organic & Biomolecular Chemistry 19, no. 8 (2021): 1732–37. http://dx.doi.org/10.1039/d0ob02386h.

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Investigation on the dynamic processes of 1-(C<sub>5</sub>H<sub>5</sub>)Si(Me)<sub>3</sub> in its Diels–Alder addition showed that Si(Me)<sub>3</sub> migration is the dominant factor and hydrogen shifts are negligible.

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