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Journal articles on the topic 'Ene reaction chemistry'

Author: Grafiati

Published: 4 June 2021

Last updated: 1 February 2022

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1

Bakhtiari, Atefeh, and Javad Safaei-Ghomi. "Effects of Chiral Ligands on the Asymmetric Carbonyl-Ene Reaction." Synlett 30, no. 15 (2019): 1738–64. http://dx.doi.org/10.1055/s-0037-1611875.

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The carbonyl-ene reaction is one of the most well-known reactions for C–C bond formation. Based on frontier molecular orbitals (FMO), carbonyl-ene reactions occur between the highest occupied molecular orbital (HOMO) of the ene compound bearing an active hydrogen atom at the allylic center and the lowest unoccupied molecular orbital (LUMO) of the electron-deficient enophile, which is a carbonyl compound. A high activation barrier enforces the concerted ene reaction rather than a Diels–Alder reaction at high temperature. Employing a catalytic system can eliminate defects in the ene reaction, an

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2

Niu, Dawen, and Thomas R. Hoye. "The aromatic ene reaction." Nature Chemistry 6, no. 1 (2013): 34–40. http://dx.doi.org/10.1038/nchem.1797.

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3

Corkey, Britton K., and F. Dean Toste. "Catalytic Enantioselective Conia-Ene Reaction." Journal of the American Chemical Society 127, no. 49 (2005): 17168–69. http://dx.doi.org/10.1021/ja055059q.

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4

Bintz-Giudicelli, C., and D. Uguen. "Ene Reaction of Allenic Sulfones." Tetrahedron Letters 38, no. 17 (1997): 2973–76. http://dx.doi.org/10.1016/s0040-4039(97)00536-4.

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5

NAGAI, Takabumi, and Itsumaro KUMADAKI. "Ene Reaction of Trifluoromethyl Carbonyl Compounds." Journal of Synthetic Organic Chemistry, Japan 49, no. 7 (1991): 624–35. http://dx.doi.org/10.5059/yukigoseikyokaishi.49.624.

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6

Huang, Shahua, Huaxing Huo, Wenhua Li, and Ran Hong. "Research Progress on Nitroso-ene Reaction." Chinese Journal of Organic Chemistry 32, no. 10 (2012): 1776. http://dx.doi.org/10.6023/cjoc201207026.

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7

Saha, Pipas, and Anil K. Saikia. "Ene cyclization reaction in heterocycle synthesis." Organic & Biomolecular Chemistry 16, no. 16 (2018): 2820–40. http://dx.doi.org/10.1039/c8ob00429c.

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8

Mackewitz, Thomas W., and Manfred Regitz. "The Ene Reaction in the Chemistry of Low-Coordinate Phosphorus." Synthesis 1998, no. 02 (1998): 125–38. http://dx.doi.org/10.1055/s-1998-2007.

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9

Trinchera, Piera, Weitao Sun, Jane E. Smith, David Palomas, Rachel Crespo-Otero, and Christopher R. Jones. "Intermolecular Aryne Ene Reaction of Hantzsch Esters: Stable Covalent Ene Adducts from a 1,4-Dihydropyridine Reaction." Organic Letters 19, no. 17 (2017): 4644–47. http://dx.doi.org/10.1021/acs.orglett.7b02272.

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10

Jayanth, Thiruvellore Thatai, Masilamani Jeganmohan, Mu-Jeng Cheng, San-Yan Chu, and Chien-Hong Cheng. "Ene Reaction of Arynes with Alkynes." Journal of the American Chemical Society 128, no. 7 (2006): 2232–33. http://dx.doi.org/10.1021/ja058418q.

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11

Guterman, Ryan, Elizabeth R. Gillies, and Paul J. Ragogna. "Phosphane–ene chemistry: the reactivity of air-stable primary phosphines and their compatibility with the thiol–ene reaction." Dalton Transactions 44, no. 35 (2015): 15664–70. http://dx.doi.org/10.1039/c5dt02364e.

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12

Houminer, Yoram, Robert A. Fenner, Henry V. Secor, and Jeffrey I. Seeman. "Steric effects on pyrolysis reactions. Thermal retro-ene reaction of pyrazineethanols." Journal of Organic Chemistry 52, no. 18 (1987): 3971–74. http://dx.doi.org/10.1021/jo00227a005.

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13

Du, Hong, Guangyu Zha, Lilong Gao, et al. "Fully biodegradable antibacterial hydrogels via thiol–ene “click” chemistry." Polym. Chem. 5, no. 13 (2014): 4002–8. http://dx.doi.org/10.1039/c4py00030g.

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Novel biodegradable antimicrobial hydrogels, which are promising for use as biomaterials, were prepared facilely via a thiol–ene “click” reaction under human physiological conditions using multifunctional poly(ethylene glycol) (PEG) derivatives as precursors.

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14

Guterman, Ryan, Amir Rabiee Kenaree, Joe B. Gilroy, Elizabeth R. Gillies, and Paul J. Ragogna. "Polymer Network Formation Using the Phosphane–ene Reaction: A Thiol–ene Analogue with Diverse Postpolymerization Chemistry." Chemistry of Materials 27, no. 4 (2015): 1412–19. http://dx.doi.org/10.1021/cm504784e.

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15

Roy, Sunanda, Tanya Das, Liying Zhang, and Xiao Matthew Hu. "Harnessing the maximum reinforcement of graphene oxide for poly(vinylidene fluoride) nanocomposites via polydopamine assisted novel surface modification." RSC Advances 6, no. 74 (2016): 69919–29. http://dx.doi.org/10.1039/c6ra12997h.

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16

Lu, Xin. "Can the Nitroso Ene Reaction Proceed Concertedly?" Organic Letters 6, no. 16 (2004): 2813–15. http://dx.doi.org/10.1021/ol048912j.

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17

Starflinger, Walter, Guenter Kresze, and Keith Huss. "Ene reaction mechanisms. 3. Intermolecular and intramolecular kinetic isotope effects (KIE) for some ene reactions of hetero enophiles." Journal of Organic Chemistry 51, no. 1 (1986): 37–40. http://dx.doi.org/10.1021/jo00351a006.

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18

Altintas, Ozcan, Thomas Josse, Julien De Winter, et al. "Ready access to end-functional polystyrenes via a combination of ARGET ATRP and thiol–ene chemistry." Polymer Chemistry 6, no. 39 (2015): 6931–35. http://dx.doi.org/10.1039/c5py01048a.

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Bromine end-groups of ATRP polystyrenes were converted into terminal alkene groupsviaa facile synthetic strategy. Subsequently, a light-induced radical thiol–ene reaction was employed for the functionalization of the terminal double bonds.

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19

Ripoll, Jean-Louis, and Yannick Vallée. "Synthetic Applications of the Retro-Ene Reaction." Synthesis 1993, no. 07 (1993): 659–77. http://dx.doi.org/10.1055/s-1993-25918.

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20

Baidya, Mahiuddin, and Hisashi Yamamoto. "Advancements in the Nascent Nitroso-Ene Reaction." Synthesis 45, no. 14 (2013): 1931–38. http://dx.doi.org/10.1055/s-0033-1339175.

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21

Alonso, Rafael, Pilar Jiménez-Meneses, Jaime García-Rupérez, María-José Bañuls, and Ángel Maquieira. "Thiol–ene click chemistry towards easy microarraying of half-antibodies." Chemical Communications 54, no. 48 (2018): 6144–47. http://dx.doi.org/10.1039/c8cc01369a.

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22

Adam, Waldemar, and Markus J. Richter. "Regioselectivity of the Singlet Oxygen Ene Reaction (Schenck Reaction) with Vinylsilanes." Journal of Organic Chemistry 59, no. 12 (1994): 3335–40. http://dx.doi.org/10.1021/jo00091a020.

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23

Manojkumar, T. K. "A computational study of ene reaction." Journal of Molecular Structure: THEOCHEM 909, no. 1-3 (2009): 96–101. http://dx.doi.org/10.1016/j.theochem.2009.05.034.

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24

Zhang, Xiaoning, Jianwei Liang, Zhenyu Chen, Carrie Donley, Xiaolin Zhang, and Guotao Cheng. "Surface Modification of Bombyx mori Silk Fibroin Film via Thiol-ene Click Chemistry." Processes 8, no. 5 (2020): 498. http://dx.doi.org/10.3390/pr8050498.

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The purpose of this work is to develop a strategy for the surface modification of Bombyx mori silk fibroin (SF) film, via a thiol-ene click reaction, in order to expand its potential applicability. To achieve this goal, terminal thiol groups, from reduced glutathione, were introduced onto the surface of the SF film via a carbodiimide coupling reaction. These immobilized thiol groups act as robust crosslinkers and allow us to rapidly functionalize the surface with alkene group-containing molecules via ultraviolet (UV) light-initiated thiol-ene click chemistry. The X-ray photoelectron spectrosco

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25

Fischmeister, Cédric, and Christian Bruneau. "Ene–yne cross-metathesis with ruthenium carbene catalysts." Beilstein Journal of Organic Chemistry 7 (February 4, 2011): 156–66. http://dx.doi.org/10.3762/bjoc.7.22.

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Conjugated 1,3-dienes are important building blocks in organic and polymer chemistry. Enyne metathesis is a powerful catalytic reaction to access such structural domains. Recent advances and developments in ene–yne cross-metathesis (EYCM) leading to various compounds of interest and their intermediates, that can directly be transformed in tandem procedures, are reviewed in this article. In addition, the use of bio-resourced olefinic substrates is presented.

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26

ADAM, W., and B. NESTLER. "ChemInform Abstract: Regio- and Diastereoselective Ene Reaction of 1O2 (Schenck Reaction) for Preparative Organic Chemistry." ChemInform 26, no. 28 (2010): no. http://dx.doi.org/10.1002/chin.199528288.

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27

Kim, Sung-Kyu, Jung-Gyen Moon, Sang-Gyeong Lee, et al. "Retro-ene reactionI: Reaction ofN-hydroxymethylsaccharin with benzoyl chlorides and alkyl halides." Journal of Heterocyclic Chemistry 30, no. 2 (1993): 353–56. http://dx.doi.org/10.1002/jhet.5570300210.

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28

Achmatowicz, Osman, Jacek Rozwadowski, Barbara Szechner, and Jan Szymoniak. "Lewis acid catalysis of the ene addition of dimethyl oxomalonate and butyl glyoxylate to olefins: Formation of cyclic ethers and lactones." Collection of Czechoslovak Chemical Communications 56, no. 5 (1991): 1011–18. http://dx.doi.org/10.1135/cccc19911011.

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The Lewis acid (SnCl4, TiCl4) catalyzed ene addition of dimethyl oxomalonate and butyl glyoxylate to pent-1-ene and 3-methylbut-1-ene has been investigated. Side reactions have been noted leading variously to the formation of δ-lactones and/or cyclic esters (tetrahydrofurans). The effect on the reaction course of the structure of the substrates has been discussed.

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29

Abu-El-Halawa, Rajab. "On the Reaction of Cyanamides with N-Alkylnitrilium and N,N-Dialkylcyanamidium Salts." Zeitschrift für Naturforschung B 64, no. 3 (2009): 297–306. http://dx.doi.org/10.1515/znb-2009-0308.

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N-Alkylnitrilium and N,N-dialkylcyanamidium salts 1 and 2 undergo ene reactions with cyanamides 4 to afford 2-azoniaallene salts 7 and 9 in which the N-alkylnitrilium salts 1 react as the ene, and the cyanamides 4 react as the enophile components. Competing with the ene reaction, N-alkylnitrilium salts 1 undergo [2++2+2] cycloaddition to furnish triazinium salts 8. 2-Azoniaallene salts react with alcohols to afford alkoxy amino derivatives 10 and 12, which yield iminium salts 11 and ketals/acetals upon further reaction with alcohols. The constitution of the 2-azoniaallene 7 and 9 and triaziniu

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30

Wiberg, Nils, Susanne Wagner, Sham-Kumar Vasisht, and Kurt Polborn. "Adducts of sila-, germa-, and stannaethenes Me2E=C(SiMe3)2 (E = Si, Ge, Sn) with anthracene: syntheses, structures, thermolyses." Canadian Journal of Chemistry 78, no. 11 (2000): 1412–20. http://dx.doi.org/10.1139/v00-095.

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The [4 + 2] cycloadducts of Me2E=C(SiMe3)2 (E = Si, Ge, Sn) and anthracene are prepared by reaction of an excess of anthracene in benzene with the [2 + 2] cycloadduct of Me2Si=C(SiMe3)2 and Ph2C=NSiMe3 at 130°C, with Me2Ge(OPh)-CLi(SiMe3)2 at 100°C, and with Me2SnBr-CNa(SiMe3)2 at 80°C, respectively. The mentioned adducts act as sources for the ethenes Me2E=C(SiMe3)2 above 100°C, the intermediate formation of which has been demonstrated by trapping experiments with 2,3-dimethylbutadiene (formation of a [4 + 2] and an ene reaction product). The half life time of the anthracene adducts with E =

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31

Radl, S. V., C. Schipfer, S. Kaiser, et al. "Photo-responsive thiol–ene networks for the design of switchable polymer patterns." Polymer Chemistry 8, no. 9 (2017): 1562–72. http://dx.doi.org/10.1039/c7py00055c.

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32

Naruse, Yuji, Tomoharu Suzuki, and Satoshi Inagaki. "Geminal bond participation in Alder ene reaction." Tetrahedron Letters 46, no. 40 (2005): 6937–40. http://dx.doi.org/10.1016/j.tetlet.2005.07.166.

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33

Platnich, Casey M., Abhinandan Banerjee, Vinayaraj Ozhukil Kollath, Kunal Karan, and Simon Trudel. "Thiol-ene click microcontact printing of gold nanoparticles onto silicon surfaces." Canadian Journal of Chemistry 96, no. 2 (2018): 190–95. http://dx.doi.org/10.1139/cjc-2017-0321.

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We report a novel process to selectively pattern nanomaterials, specifically gold nanoparticles, onto a silicon surface through “click” chemistry, to consistently and efficiently join together small units through a quick and simple reaction. We employed the UV-initiated thiol-ene reaction, which is used in tandem with microcontact printing. Dithiol-capped nanoparticles were used as a printing ink and were grafted onto ene-terminated Si(100) wafers by pressing a nanoparticle-impregnated poly(dimethylsiloxane) stamp, while irradiating with ultraviolet light to activate a radical initiator. The r

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34

Kamimura, Akio, та Akinori Yamamoto. "Diastereoselective Ene Reaction of 3-Formyl-Δ2-isoxazolines". Chemistry Letters 19, № 11 (1990): 1991–94. http://dx.doi.org/10.1246/cl.1990.1991.

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35

Majik, Mahesh S., Peruninakulath S. Parameswaran, and Santosh G. Tilve. "Tandem Wittig−Ene Reaction Approach to Kainic Acid." Journal of Organic Chemistry 74, no. 9 (2009): 3591–94. http://dx.doi.org/10.1021/jo900196t.

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36

Cao, Weidi, and Xiaohua Liu. "Asymmetric Formal Hetero-Ene Reaction of Allylgold Intermediates." Chinese Journal of Organic Chemistry 41, no. 2 (2021): 857. http://dx.doi.org/10.6023/cjoc202100009.

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37

Lee, Gon-Ann, Chaur-Shenq Shiau, Chi-Sheng Chen, and Jay Chen. "Regioselectivity of the Ene Reaction: Dimerization of 8-Chlorobicyclo[5.1.0]oct-1(8)-ene." Journal of Organic Chemistry 60, no. 11 (1995): 3565–67. http://dx.doi.org/10.1021/jo00116a055.

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38

Khan, Ezzat, and Bernd Wrackmeyer. "Synthesis, NMR characterization and reactivity of 1-silacyclohex-2-ene derivatives." Open Chemistry 10, no. 5 (2012): 1633–39. http://dx.doi.org/10.2478/s11532-012-0079-1.

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AbstractThe chloro functionality of allyldichlorosilane (HSiCl2(C3H5)) and allyldichloromethylsilane (MeSiCl2(C3H5)) were replaced by alkynyl groups and new compounds, allyldialkynylsilane 1 and allyldialkynylmethylsilane 2, were obtained. These silanes, which served as starting materials for the onward reactions, were purified by fractional distillation. They were further subjected to hydroboration with 9-BBN (9-borabicyclo[3.3.1]nonane) and were converted into 1-silacyclohex-2-ene derivatives 5 and 6. The competition between C≡C and C=C in the reaction was studied. The hydroborating reagent

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39

Candito, David A., Jane Panteleev, and Mark Lautens. "Intramolecular Aryne–Ene Reaction: Synthetic and Mechanistic Studies." Journal of the American Chemical Society 133, no. 36 (2011): 14200–14203. http://dx.doi.org/10.1021/ja205405n.

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40

Yamazaki, Shoko, Junya Wada, and Kiyomi Kakiuchi. "Stereospecific cyclization reaction of alkenyl esters and amides of ethenetricarboxylate." Canadian Journal of Chemistry 93, no. 10 (2015): 1122–31. http://dx.doi.org/10.1139/cjc-2015-0129.

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The stereospecificity of the cyclization reaction of (E)- and (Z)-2-alkenyl esters and amides of ethenetricarboxylate has been examined. The reaction of (E)/(Z)-2-butenyl esters with AlCl3 or FeCl3 gave trans-substituted chlorinated γ-lactone diastereomers stereospecifically. (E)/(Z)-2-butenyl and pentenyl amides undergo an intramolecular ene reaction at room temperature gradually. At 80 °C, the (Z)-alkenyl amides were transformed to cis-substituted ene adducts and the (E)-amides were transformed to cis- and trans-substituted ene adduct mixtures. The reaction of (E)/(Z)-2-alkenyl amides with Z

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41

Malakar, Tanmay, and Paul M. Zimmerman. "Brønsted-Acid-Catalyzed Intramolecular Carbonyl–Olefin Reactions: Interrupted Metathesis vs Carbonyl-Ene Reaction." Journal of Organic Chemistry 86, no. 3 (2021): 3008–16. http://dx.doi.org/10.1021/acs.joc.0c03021.

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42

Harmata, Michael, Chaofeng Huang, Parham Rooshenas, and Peter R Schreiner. "An Interrupted [4+3] Cycloaddition Reaction: A Hydride Shift (Ene Reaction) Intervenes." Angewandte Chemie International Edition 47, no. 45 (2008): 8696–99. http://dx.doi.org/10.1002/anie.200803487.

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43

Nair, C. P. Reghunadhan, and K. N. Ninan. "Phosphazene-Triazine Polymers by Alder-ene Reaction." Polymers and Polymer Composites 12, no. 1 (2004): 55–62. http://dx.doi.org/10.1177/096739110401200105.

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44

Werstiuk, Nick Henry, and Wojciech Sokol. "Density functional theory computational study on Diels–Alder reactions of cyclopentadiene with selected vinylsilanes and methylenecyclopropane." Canadian Journal of Chemistry 89, no. 3 (2011): 409–14. http://dx.doi.org/10.1139/v10-167.

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Aimed at predicting relative reactivities, density functional theory (DFT) calculations were carried out on a series of Diels–Alder reactions involving silylvinyl derivatives reacting with cyclopentadiene as part of a synthetic research project. Using three reactions for which experimental rate data are available to calibrate our calculations, we computationally pinpointed the best synthetic route to bicyclo[2.2.1]hept-5-ene-2,2-diylbis(trimethylsilane) (1). The synthesis begins with the Diels–Alder reaction of cyclopentadiene (2) with commercially available (1-bromovinyl)trimethylsilane (6).

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45

Qian, Changtao, and Taisheng Huang. "Glyoxylate-Ene Reaction Catalyzed by Ln(OTf)3." Tetrahedron Letters 38, no. 38 (1997): 6721–24. http://dx.doi.org/10.1016/s0040-4039(97)01536-0.

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46

Fang, Fang, Fang Xie, Han Yu, Hui Zhang, Bo Yang, and Wanbin Zhang. "Efficient bimetallic titanium catalyst for carbonyl-ene reaction." Tetrahedron Letters 50, no. 48 (2009): 6672–75. http://dx.doi.org/10.1016/j.tetlet.2009.09.078.

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47

Hatakeyama, Susumi. "Indium-catalyzed Conia-ene reaction for alkaloid synthesis." Pure and Applied Chemistry 81, no. 2 (2009): 217–26. http://dx.doi.org/10.1351/pac-con-08-07-14.

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In(OTf)3-catalyzed cyclization of nitrogen- and oxygen-tethered acetylenic malonic esters provides various five- to seven-membered heterocycles in moderate to excellent yield, and the reaction proceeds with no racemization and complete E-selectivity in the case of chiral and nonterminal alkynes. The synthetic utility is demonstrated by the synthesis of (-)-salinosporamide A, a highly potent 20S proteasome inhibitor, and (+)-neooxazolomycin, a member of the oxazolomycin family of antibiotics.

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48

Hase, T., G. Brunow, A. Hase, et al. "Search for antibody catalysts for the ene reaction." Pure and Applied Chemistry 68, no. 3 (1996): 605–8. http://dx.doi.org/10.1351/pac199668030605.

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49

Tong, Juliana T. W., Iman Kavianinia, Scott A. Ferguson, Gregory M. Cook, Paul W. R. Harris, and Margaret A. Brimble. "Synthesis of paenipeptin C′ analogues employing solution-phase CLipPA chemistry." Organic & Biomolecular Chemistry 18, no. 23 (2020): 4381–85. http://dx.doi.org/10.1039/d0ob00950d.

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50

Sakumo, Kunihiro, Noriko Kuki, Terumi Kuno, et al. "Ene-type reaction of trifluoroacetaldehyde hemiacetal with ene compounds in the presence of a Lewis acid." Journal of Fluorine Chemistry 93, no. 2 (1999): 165–70. http://dx.doi.org/10.1016/s0022-1139(98)00291-7.

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