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Journal articles on the topic 'Ene reaction'

Author: Grafiati

Published: 4 June 2021

Last updated: 7 September 2023

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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 (July 23, 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, and chiral catalysts promote the reaction under mild conditions to produce optically active compounds. In this account, we highlight investigations on the effects of various classes of chiral ligands on intermolecular and intramolecular carbonyl-ene reactions.1 Introduction2 Biaryl-Type Chiral Ligands3 C 1- and C 2-Symmetric Bis(oxazoline) Ligands4 Schiff Base Ligands5 N,N′-Dioxide Ligands6 Conclusions

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2

Clarke, Matthew L., and Marcia B. France. "The carbonyl ene reaction." Tetrahedron 64, no. 38 (September 2008): 9003–31. http://dx.doi.org/10.1016/j.tet.2008.06.075.

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3

Cossy, J., A. Bouzide, and M. Pfau. "Asymmetric intramolecular Ene-reaction." Tetrahedron Letters 33, no. 34 (August 1992): 4883–84. http://dx.doi.org/10.1016/s0040-4039(00)61223-6.

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4

Niu, Dawen, and Thomas R. Hoye. "The aromatic ene reaction." Nature Chemistry 6, no. 1 (November 17, 2013): 34–40. http://dx.doi.org/10.1038/nchem.1797.

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5

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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6

Lee, Chi-Sing, Guangyan Du, Gaopeng Wang, Wenjing Ma, Qianqian Yang, Wenli Bao, Xuefeng Liang, and Lizhi Zhu. "Syntheses of Diverse Natural Products via Dual-Mode Lewis Acid Induced Cascade Cyclization Reactions." Synlett 28, no. 12 (April 6, 2017): 1394–406. http://dx.doi.org/10.1055/s-0036-1588777.

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The σ/π-binding properties of a series of Lewis acids was studied using DFT calculations. The results led to the identification of Zn(II)/In(III) as a suitable dual-mode Lewis acid for use in promoting cascade cyclization reactions. Based on this finding, we developed three new types of dual-mode Lewis acid induced cascade cyclization reactions and have demonstrated the utilities of each process in natural product synthesis.1 Introduction2 Dual-Mode Lewis Acids3 Prins/Conia-Ene Cascade Reaction and its Applications4 Diels–Alder/Carbocyclization Cascade Reaction and Applications4.1 First Generation Diels–Alder/Carbocyclization Cascade Reaction and its Application4.2 Second Generation Diels–Alder/Carbocyclization Cascade Reaction and its Applications5 Michael/Conia-Ene Cascade Reaction and its Applications6 Conclusion

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7

Kanase, Vanita, and Diptesh T Patil. "EVALUATION OF IN VIVO IMMUNOMODULATORY ACTIVITY OF AQUEOUS AND ETHANOLIC EXTRACT OF EULOPHIA NUDA L." Asian Journal of Pharmaceutical and Clinical Research 11, no. 12 (December 7, 2018): 374. http://dx.doi.org/10.22159/ajpcr.2018.v11i12.27051.

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Objective: The aim of this study was to evaluate the in vivo immunomodulatory activity of an aqueous and ethanolic extract of dried tubers of Eulophia nuda (ENA and ENE).Methods: Effect of both the extracts was evaluated on delayed-type hypersensitivity (DTH) response, serum antibody response, and cyclophosphamide-induced myelosuppression in Swiss albino mice.Results: The extracts showed stimulation of DTH reaction in mice in response to T-cell dependent antigen by both ENE () and ENA (); significant increase in serum antibody titer at of ENA (768.01) and ENE (768.33) extract at 200 mg/kg, compared to control group (213.33); Combined treatment of ENA+Cytochromes P450 [CYP]-25 mg/kg and ENE+CYP-25mg/kg (50, 100, and 200 mg/kg) doses of ENA and ENE each with 25 mg/kg resulted in restoration of bone marrow activity as compared with CYP treatment alone.Conclusion: Both specific and non-specific immunostimulating properties of the ENE and ENA tubers in in vivo experimental methods suggest its therapeutic usefulness in immunocompromised conditions.

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8

Ollevier, Thierry, and Di Meng. "Fe(BF4)2-Catalyzed Inter- and Intramolecular Carbonyl-Ene Reaction of Trifluoropyruvate." Synlett 29, no. 05 (December 13, 2017): 640–44. http://dx.doi.org/10.1055/s-0036-1591858.

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Inter- and intramolecular carbonyl-ene reactions have been developed using 5 mol% Fe(BF4)2 as catalyst, affording homoallylic alcohols in 36–87% isolated yields. This catalyst, prepared from FeCl2 and AgBF4, is the first FeII Lewis acid reported for the carbonyl-ene reaction using ethyl trifluoropyruvate. The method was successfully applied to the reaction of various 1,1-disubstituted alkenes with ethyl trifluoropyruvate and to the cyclization of citronellal.

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9

Terada, M., K. Machioka, and K. Sorimachi. "Enantioselective Aza-Ene-Type Reaction." Synfacts 2006, no. 5 (May 2006): 0500. http://dx.doi.org/10.1055/s-2006-934450.

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10

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

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11

Ohashi, Masao, Cooper S. Jamieson, Yujuan Cai, Dan Tan, Daiki Kanayama, Man-Cheng Tang, Sarah M. Anthony, et al. "An enzymatic Alder-ene reaction." Nature 586, no. 7827 (September 30, 2020): 64–69. http://dx.doi.org/10.1038/s41586-020-2743-5.

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12

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

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13

Hilt, Gerhard, and Jonas Treutwein. "Cobalt-Catalyzed Alder–Ene Reaction." Angewandte Chemie International Edition 46, no. 44 (November 12, 2007): 8500–8502. http://dx.doi.org/10.1002/anie.200703180.

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14

Desimoni, G., G. Faita, P. P. Righetti, A. Sfulcini, and D. Tsyganov. "Solvent effect in pericyclic reactions. IX. The ene reaction." Tetrahedron 50, no. 6 (January 1994): 1821–32. http://dx.doi.org/10.1016/s0040-4020(01)80854-1.

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15

Jin, Rui, Song Liu, and Yu Lan. "Distortion–interaction analysis along the reaction pathway to reveal the reactivity of the Alder-ene reaction of enes." RSC Advances 5, no. 75 (2015): 61426–35. http://dx.doi.org/10.1039/c5ra10345b.

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The reactivity of uncatalyzed Alder-ene type reactions of hetero-substituted propylene is interpreted by distortion–interaction analysis of both the transition states and the complete reaction pathways.

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16

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 (November 1, 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 = Si, Ge, and Sn in the presence of DMB (= 2,3-dimethylbutadiene) in benzene on thermolysis at 130°C (first order reactions) is found to be 141, 12, and 0.3 h, respectively. In the absence of DMB, thermolysis of the cycloadducts leads in benzene as reaction medium exclusively to the dimers of the Me2E=C(SiMe3)2 intermediates. In toluene as reaction medium ene products of Me2E=C(SiMe3)2 are observed in addition to the dimers. The ene products are not isolable as such, but only after migration of the Me2E-CH(SiMe3)2 substituents. The formed derivatives C6H5CH2EMe2CH(SiMe3)2 of toluene in part give a second ene reaction with another Me2E=C(SiMe3)2 molecule. X-ray structure analyses of the mentioned sources in fact prove the latter to be normal [4 + 2] cycloadducts of Me2E=C(SiMe3)2 and anthracene.Key words: silaethene, germaethene, stannaethene, [4 + 2] anthracene adducts, [4 + 2] cycloadditions and reversions, ene reactions, X-ray structure analyses.

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17

Haynes, RK, AG Katsifis, LM King, and SC Vonwiller. "Aprotic Conjugate Addition Reactions of Lithiated Allylic Sulfoxides With Acyclic Enones; a Breakdown of the trans-Decalyl Transition State." Australian Journal of Chemistry 42, no. 10 (1989): 1785. http://dx.doi.org/10.1071/ch9891785.

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The reactions of lithiated 1-(t-butylsulfinyl)prop-2-ene, 1-(t-butylsulfinyl)-3-methylbut-2-ene, 1-(t-butylsulfinyl)but-2-ene, 1-(phenylsulfinyl)but-2-ene and 2-methyl-1-(phenylsu1finyl)prop- 2-ene with methyl vinyl ketone, mesityl oxide and crotonaldehyde give largely carbonyl addition products arising from reaction through C1 or C3 of the allyl system. In the case of methyl crotonate, conjugate addition through C3 is observed. The initially formed diastereomers of the C1 adducts, allylic sulfoxides, are configurationally unstable. Only the lithiated 1-(t-butylsulfinyl)-3-methylbut-2-ene undergoes conjugate addition with methyl vinyl ketone to give an (E)-vinyl sulfoxide whose formation may involve the trans-decalyl transition state characteristic of the reactions of lithiated allylic sulfoxides with cyclic enones.

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18

Abu-El-Halawa, Rajab. "On the Reaction of Cyanamides with N-Alkylnitrilium and N,N-Dialkylcyanamidium Salts." Zeitschrift für Naturforschung B 64, no. 3 (March 1, 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 triazinium salts 8 was secured by elemental analyses and spectral properties (IR and NMR).

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19

Susan, M. A. B. H., G. Ara, M. M. Islam, M. M. Rahman, and M. Y. A. Mollah. "Thin Layer Chromatography-A Tool to Investigate Kinetics of Michael Addition Reaction." Journal of Scientific Research 10, no. 3 (September 1, 2018): 323–29. http://dx.doi.org/10.3329/jsr.v10i3.37190.

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Thin layer chromatography (TLC), a tool for defining identity, purity, and quantitation of a compound, has also been proved useful for monitoring the progress of a chemical reaction. However, the technique is yet to be exploited for investigating the kinetics of a reaction systematically. In this work, we used TLC for measuring the time for consumption of a reactant in Michael addition reaction of acetylacetone with 2-cyclohexene-1-one. Average rate of the model reaction was determined using a definite initial concentration of acetylacetone for a series of catalyst systems like NaOH, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), DBU based protic ionic liquids (PILs) 1,8-diazabicyclo[5.4.0]undec-7-ene-8-ium hydroxide ([HDBU]OH) and 1,8-diazabicyclo[5.4.0]undec-7-ene-8-ium acetate ([HDBU]CH3COO), a DBU based aprotic ionic liquid (AIL), 8-hexyl-1,8-diazabicyclo [5.4.0]undec-7-ene-8-ium hydroxide ([C6DBU]OH), and binary systems of the ionic liquids with molecular solvents, such as, water, DBU, and acetic acid. The kinetic data on the performance of the chosen catalysts were interpreted on the basis of the established mechanism of the reaction. Finally, the prospect of the method based on TLC as a suitable technique for kinetic study of chemical reactions has been discussed.

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20

Kafka, Zdeněk, and Luděk Vodička. "The Diels-Alder reaction of butadiene with hexacyclic olefins in the synthesis of triamantane." Collection of Czechoslovak Chemical Communications 51, no. 5 (1986): 1083–85. http://dx.doi.org/10.1135/cccc19861083.

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The paper describes the composition of products arising from the Diels-Alder reaction of butadiene with hexacyclic olefins (hexacyclo[8,4,0,02,7,03,14,04,8,09,13]tetradec-5-ene and hexacyclo[6,6,0,02,6,05,14,07,12,09,13]tetradec-3-ene) under different conditions. The reaction afforded a mixture of heptacyclic olefins (heptacyclo[8,8,0,02,17,03,11,04,9,012,16,013,18]octadec-6-ene and heptacyclo[8,8,0,02,13,03,11,04,9,012,17,014,18]octadec-6-ene), which is an important intermediate in the synthesis of triamantane.

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21

Yamazaki, Shoko, Junya Wada, and Kiyomi Kakiuchi. "Stereospecific cyclization reaction of alkenyl esters and amides of ethenetricarboxylate." Canadian Journal of Chemistry 93, no. 10 (October 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 ZnI2 gave trans-substituted γ-lactam diastereomers stereospecifically along with the ene adducts.

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22

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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23

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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24

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

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25

Motoki, Shinichi, Tsumoru Watanabe, and Takao Saito. "Intramolecular ene reaction of unsaturated thioketones." Tetrahedron Letters 30, no. 2 (January 1989): 189–92. http://dx.doi.org/10.1016/s0040-4039(00)95156-6.

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26

Mikami, Koichi, Masahiro Terada, Satoshi Narisawa, and Takeshi Nakai. "Asymmetric Catalysis for Carbonyl-Ene Reaction." Synlett 1992, no. 04 (1992): 255–65. http://dx.doi.org/10.1055/s-1992-21333.

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27

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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28

Achmatowicz, Osman, and Ewa Bialecka-Florjańczyk. "Mechanism of the carbonyl-ene reaction." Tetrahedron 52, no. 26 (June 1996): 8827–34. http://dx.doi.org/10.1016/0040-4020(96)00424-3.

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29

SHIMADA, Tetsuo, Akira ANDO, Toshiyuki TAKAGI, Mayumi KOYAMA, Takuichi MIKI, and Itsumaro KUMADAKI. "Ene reaction of N-tosylhexafluoroacetone imine." CHEMICAL & PHARMACEUTICAL BULLETIN 40, no. 6 (1992): 1665–66. http://dx.doi.org/10.1248/cpb.40.1665.

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30

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 (February 2006): 2232–33. http://dx.doi.org/10.1021/ja058418q.

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31

Povie, Guillaume, Anh-Tuan Tran, David Bonnaffé, Jacqueline Habegger, Zhaoyu Hu, Christine Le Narvor, and Philippe Renaud. "Repairing the Thiol-Ene Coupling Reaction." Angewandte Chemie 126, no. 15 (March 11, 2014): 3975–79. http://dx.doi.org/10.1002/ange.201309984.

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32

Niu, Dawen, and Thomas R. Hoye. "ChemInform Abstract: The Aromatic Ene Reaction." ChemInform 45, no. 27 (June 20, 2014): no. http://dx.doi.org/10.1002/chin.201427039.

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33

COSSY, J., A. BOUZIDE, and M. PFAU. "ChemInform Abstract: Asymmetric Intramolecular Ene Reaction." ChemInform 24, no. 1 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199301175.

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34

Povie, Guillaume, Anh-Tuan Tran, David Bonnaffé, Jacqueline Habegger, Zhaoyu Hu, Christine Le Narvor, and Philippe Renaud. "Repairing the Thiol-Ene Coupling Reaction." Angewandte Chemie International Edition 53, no. 15 (March 11, 2014): 3894–98. http://dx.doi.org/10.1002/anie.201309984.

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35

Teo, Yew Chin, Yuanhang Pan, and Choon Hong Tan. "Organic Dye-Photocatalyzed Acylnitroso Ene Reaction." ChemCatChem 5, no. 1 (October 12, 2012): 235–40. http://dx.doi.org/10.1002/cctc.201200435.

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36

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 (August 17, 2017): 4644–47. http://dx.doi.org/10.1021/acs.orglett.7b02272.

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37

Gille, Austin L., Staci E. Hammer, Jenna M. Lafferty, Keaton R. Lawson, James R. Gustafson, Brendan C. Dutmer, and Thomas M. Gilbert. "Computational studies of ene reactions between aminoborane (F3C)2BN(CH3)2 and substituted propenes: additive effects on barriers and reaction energies." Dalton Transactions 48, no. 23 (2019): 8161–74. http://dx.doi.org/10.1039/c9dt01333d.

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38

Skattebøl, Lars, Yngve Stenstrøm, and Einar Uggerud. "A Study on the Nature of the Allene-ene Intramolecular Cycloaddition Reaction. A Novel Allene-ene Reaction." Acta Chemica Scandinavica 40b (1986): 363–69. http://dx.doi.org/10.3891/acta.chem.scand.40b-0363.

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39

Marples, Brian A., and Christopher D. Spilling. "The ene reaction of 5-allyl-2ϵ-hydroxy-5α-cholestan-3-one: An unusually facile ene reaction." Tetrahedron Letters 28, no. 5 (January 1987): 581–84. http://dx.doi.org/10.1016/s0040-4039(00)95787-3.

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40

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 (February 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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41

Naka, Akinobu, Jun Sakata, Junnai Ikadai, Hiroyuki Kawasaki, Joji Ohshita, Eigo Miyazaki, Atsutaka Kunai, Kazunari Yoshizawa, and Mitsuo Ishikawa. "Stereochemistry of Disilanylene-containing Cyclic Compounds – Synthesis and Palladium-catalyzed Reactions of cis- and trans-3,4- Benzo-1,2-diisopropyl-1,2-dimethyl-1,2-disilacyclobut-3-ene." Zeitschrift für Naturforschung B 64, no. 11-12 (December 1, 2009): 1580–90. http://dx.doi.org/10.1515/znb-2009-11-1243.

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The synthesis and palladium-catalyzed reactions of cis- and trans-3,4-benzo-1,2-diisopropyl- 1,2-dimethyl-1,2-disilacyclobut-3-ene (1a and 1b) are reported. Their reactions with diphenylacetylene in the presence of a catalytic amount of tetrakis(triphenylphosphine)palladium(0) proceeded with high stereospecificity to give cis- and trans-5,6-benzo-1,4-diisopropyl-1,4-dimethyl- 2,3-diphenyl-1,4-disilacyclohexa-2,5-diene, 2a and 2b, in 95% and 93% yield, respectively. Similar palladium-catalyzed reactions of 1a and 1b with monosubstituted acetylenes, such as 1-hexyne, tert-butylacetylene, phenylacetylene, and trimethylsilylacetylene, also proceeded stereospecifically to afford the respective cis- and trans-5,6-benzo-1,4-disilacyclohexa-2,5-dienes, 3a - 6a and 3b - 6b, in excellent yields and as the sole products. The palladium-catalyzed reaction of 1a with styrene gave a mixture consisting of two stereoisomers, cis-2- and trans-2-phenyl-substituted 5,6- benzo-(r-1),cis-4-diisopropyl-1,4-disilacyclohex-5-ene 7a and 8a in a ratio of 5 : 3 in 72% combined yield, while the reaction of styrene with 1b afforded two stereoisomers, 7b and 8b, in a ratio of 2 : 1 in 80% combined yield. With 1-hexene, 1a gave two stereoisomers, 5,6-benzo-cis-2-(nbutyl)-( r-1),cis-4-diisopropyl- and 5,6-benzo-trans-2-(n-butyl)-(r-1),cis-4-diisopropyl-1,4-dimethyl- 1,4-disilacyclohex-5-ene, 9a and 10a, in a ratio of 1 : 1 in 70% combined yield. A similar reaction of 1b with 1-hexene produced 5,6-benzo-cis-2-(n-butyl)-(r-1),trans-4-diisopropyl-1,4-dimethyl-1,4- disilacyclohex-5-ene in 81% yield and as a single isomer

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42

TAKAGUCHI, YUTAKA, TAKAAKI TSUBOI, YUUKI SAKO, and SADAO TSUBOI. "SYNTHESIS OF FULLERODENDRON AND ITS PHOTOCATALITIC ACTIVITY." International Journal of Nanoscience 05, no. 04n05 (August 2006): 593–97. http://dx.doi.org/10.1142/s0219581x0600484x.

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A newly designed fullerodendron was synthesized in good yield (84%) by the use of a Diels-Alder reaction of C 60 with an anthryl dendron. Interestingly, the fullerodendron acts as a new catalyst that uses oxygen and light to generate singlet oxygen (1 O 2). The dendron facilitates various types of singlet oxygenation reactions including ene reaction, Diels-Alder reaction, and oxidation of phenol and sulfide.

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43

Wiberg, N., G. Preiner, G. Wagner, and H. Köpf. "Reaktivität des labilen, durch Adduktbildung mit Ph2C=NSiMe3 gespeicherten Silaethens Me2Si=C(SiMe3)2 / Reactivity of the Labile Silaethene Me2Si = C(SiMe3)2, Stored as Ph2C =NSiMe3 Adducts." Zeitschrift für Naturforschung B 42, no. 9 (September 1, 1987): 1062–74. http://dx.doi.org/10.1515/znb-1987-0902.

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Silaethene Me2Si = C(SiMe3)2 (1), stored as Ph2C=NSiMe3 adducts and regenerated from the adducts at about 100 °C as a reaction intermediate, combines with reactants a-b (e. g. HO-H, RO-H. RCOO-H, RS-H. RHN-H, Ph2CN-H, RO-SiR3, R2N-SiR3, Ph2CN-SiR3, Cl-GeR3, Cl-SnR3) with insertion into the a-b bond, with a=b (e.g. 0 = CPh2, Me3SiN = CPh2, CH2=CHOMe, cis-piperylene), a=b=c (e.g. RN = N = N, O = N=N). a=b-c=d (e.g. butadiene, isoprene, trans-piperylene, 2,3-dimethylbutadiene, cyclopentadiene, anthracene, benzophenone, N-trimethylsilylbenzophenoneimine) under [2+2]-, [2+3]- as well as [2+A]-cycloaddition and with a=b-c-H (e.g. propene, butenes, isoprene. 2.3-dimethylbutadiene, acetone) under ene reaction. According to relative reaction rates, insertion and [2+2]-cycloadditions seem to proceed in two reaction steps, whereas [2+4]-cycloadditions and ene reactions with organic dienes and enes obviously are one step reactions. For relative reactivities cf. Table I.

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44

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 (September 1987): 3971–74. http://dx.doi.org/10.1021/jo00227a005.

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45

Elemes, Yiannis, Manolis Stratakis, and Michael Orfanopoulos. "Reactions of triazolinediones with cis-alkenes. A highly regioselective ene reaction." Tetrahedron Letters 30, no. 49 (January 1989): 6903–6. http://dx.doi.org/10.1016/s0040-4039(01)93384-2.

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46

Taylor, Richard T., and Dhruba P. Poudel. "Thiol-Ene Reaction of Heparin Allyl Ester, Heparin 4-Vinylbenzyl Ester and Enoxaparin." Reactions 3, no. 3 (September 5, 2022): 442–50. http://dx.doi.org/10.3390/reactions3030031.

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Heparin allyl ester and heparin 4-vinylbenzyl ester were prepared and examined for their potential for thiol-ene reaction using both free radical initiators and photochemistry. While both undergo reaction with mercaptoacetic acid, the allyl ester adduct proved to be somewhat more labile. Several more examples of adducts from heparin 4-vinylbenzyl ester are reported. Similar reactions on enoxaparin, where the reaction site is solely at the non-reducing end of the molecule, are also reported. These reactions may show promise as a strategy in the development of drug conjugates.

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47

Shimomura, Osamu, Suguru Sasaki, Kaori Kume, Atsushi Ohtaka, and Ryôki Nomura. "Temperature-Dependent Enhancement Effects for TBD (1,5,7-Triazabicyclo[4.4.0]dec-5-ene) with 2-Methylimidazole-Intercalated α-Zirconium Phosphate as a Latent Thermal Initiator in the Reaction of Glycidyl Phenyl Ether." Inorganics 7, no. 7 (June 30, 2019): 83. http://dx.doi.org/10.3390/inorganics7070083.

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The catalytic effects of 1,1,3,3-Tetramethylguanidine (TMG), 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD), 7-Methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) in the reaction with glycidyl phenyl ether (GPE) at 40 °C were investigated. For the reaction, the %conversion of GPE was only 11%, carried out at 40 °C over 14 days in the presence of TBD.Additionally, there was little catalytic activity for the same reaction performed under typical storage conditions at 25 °C. The effect of TBD with 2-methylimidazole-intercalated α-zirconium phosphate (α-ZrP∙2MIm), as a latent thermal initiating system in the reaction with GPE, was then examined. The reaction did not proceed within 1 h at 80 °C. On increasing the temperature to 120 °C, the %conversion reached 75% for reaction at 1 h. Under typical storage conditions (7 days at 25 °C), the %conversion of GPE was only 7%. With addition of TBD to α-ZrP∙2MIm, reagent stability was maintained, and the polymerization reaction proceeded rapidly with the application of heat.

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48

Behera, Prasanta Kumar, Prithwiraj Mandal, Madhuchhanda Maiti, Raksh Vir Jasra, and Nikhil K. Singha. "INSIGHTS INTO THE PREPARATION OF VINYL POLYBUTADIENE VIA COBALT-BASED CATALYST: TUNING ITS PROPERTIES BY THIOL-ENE MODIFICATION OF VINYL GROUP." Rubber Chemistry and Technology 89, no. 2 (June 1, 2016): 335–48. http://dx.doi.org/10.5254/rct.16.84832.

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ABSTRACT Elastomers with pendant alkenyl functionality can be easily modified using different types of postpolymerization reactions that lead to improved properties. This investigation reports the preparation of polybutadiene (PB) with control vinyl content by Co-based catalyst followed by modification of vinyl functionality via thiol-ene reaction. In this case, the polymerization of butadiene was carried out in cyclohexane using cobalt octanoate (Co[oct]2) in combination with diethylaluminium chloride (DEAC) and triethylaluminium (TEAL) as cocatalysts. The effects of different parameters, such as the concentration of catalyst and cocatalyst, monomer concentration, and reaction temperature on polymerization of butadiene (BD), were evaluated and optimized to obtain the desired vinyl content in the polymer. The microstructures in PB were investigated by 1H nuclear magnetic resonance (NMR) and Fourier transform infrared spectroscopy analyses. Molecular weights and dispersity (Ð) of the polymers were determined by gel permeation chromatography analysis. The viscosity average molecular weight was calculated from the intrinsic viscosity [η] using the Mark-Houwink equation. Synthesized vinyl-PB was modified by the thiol-ene reaction using benzyl mercaptan as thiolating agent and 2,2′-azobis(isobutyronitrile) as an initiator. Thiol-ene modification was confirmed by 1H NMR analysis. Surface characteristics of thiol-modified PB were characterized by goniometer. Thiol-ene–modified PB showed greatly improved adhesive strength in metal–rubber bonding, as determined by lap shear test.

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Choudhuri, Khokan, Arkalekha Mandal, and Prasenjit Mal. "Aerial dioxygen activation vs. thiol–ene click reaction within a system." Chemical Communications 54, no. 30 (2018): 3759–62. http://dx.doi.org/10.1039/c8cc01359d.

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By choosing appropriate reaction systems using solvents with additives or solvent free neat conditions, any one of the Markovnikov or anti-Markovnikov selective thiol–ene click (TEC) reactions and the synthesis of β-hydroxysulfides via aerial dioxygen activation could be achieved exclusively in excellent yields.

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50

Protiva, Jiří, Thi Thu Huong Nguyen, Jiří Urban, and Eva Klinotová. "Reactions of 21-Acetoxy-16α,17α-epoxypregn-4-ene-3,20-dione with Nitrogen-Containing Nucleophilic Agents." Collection of Czechoslovak Chemical Communications 62, no. 7 (1997): 1095–104. http://dx.doi.org/10.1135/cccc19971095.

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21-Acetoxy-16α,17α-epoxypregn-4-ene-3,20-dione (1) enters a reaction with acetonitrile catalyzed by perchloric acid, giving unusual products with the furostane skeleton. In contrast to analogous reactions, the reaction with sodium azide results in the azido derivative possessing the non-rearranged ring D. The 1H NMR, 13C NMR, and mass spectra are discussed.

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