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Статті в журналах з теми "Diaryl Diselenides"

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Автор: Grafiati

Опубліковано: 6 вересня 2023

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1

Kobiki, Yohsuke, Shin-ichi Kawaguchi, Takashi Ohe, and Akiya Ogawa. "Photoinduced synthesis of unsymmetrical diaryl selenides from triarylbismuthines and diaryl diselenides." Beilstein Journal of Organic Chemistry 9 (June 13, 2013): 1141–47. http://dx.doi.org/10.3762/bjoc.9.127.

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Анотація:

A novel method of photoinduced synthesis of unsymmetrical diaryl selenides from triarylbismuthines and diaryl diselenides has been developed. Although the arylation reactions with triarylbismuthines are usually catalyzed by transition-metal complexes, the present arylation of diaryl diselenides with triarylbismuthines proceeds upon photoirradiation in the absence of transition-metal catalysts. A variety of unsymmetrical diaryl selenides can be conveniently prepared by using this arylation method.

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2

Perin, Gelson, Daniela Rodrigues Araujo, Patrick Carvalho Nobre, Eder João Lenardao, Raquel Guimarães Jacob, Marcio Santos Silva, and Juliano Alex Roehrs. "Ultrasound-promoted synthesis of 2-organoselanyl-naphthalenes using Oxone® in aqueous medium as an oxidizing agent." PeerJ 6 (May 7, 2018): e4706. http://dx.doi.org/10.7717/peerj.4706.

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A green methodology to synthesize 2-organoselanyl-naphthalenes based on the reaction of alkynols with diaryl diselenides is described. The electrophilic species of selenium were generated in situ, by the oxidative cleavage of the Se–Se bond of diaryl diselenides by Oxone® using water as the solvent. The reactions proceeded efficiently under ultrasonic irradiation as an alternative energy source, using a range of alkynols and diorganyl diselenides as starting materials. Through this methodology, the corresponding 2-organoselanyl-naphthalenes were obtained in moderate to good yields (56–94%) and in short reaction times (0.25–2.3 h).

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3

Movassagh, Barahman, and Azadeh Fazelia. "Zinc-Mediated Synthesis of Diaryl Selenides from Diaryl Diselenides and Diaryliodonium Salts in Aqueous Media." Zeitschrift für Naturforschung B 61, no. 2 (February 1, 2006): 194–96. http://dx.doi.org/10.1515/znb-2006-0213.

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AbstractAn efficient synthetic method has been developed for the preparation of symmetrical and unsymmetrical diaryl selenides through a one-pot reaction of diaryl diselenides and diaryliodonium salts in the presence of Zn/AlCl3 system in aqueous media.

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4

Zhao, Hong, Yuanyuan Jiang, Qiurong Chen, and Mingzhong Cai. "A highly efficient and reusable MCM-41-immobilized bipyridine copper(i) catalyst for the C–Se coupling of organoboronic acids with diaryl diselenides." New Journal of Chemistry 39, no. 3 (2015): 2106–15. http://dx.doi.org/10.1039/c4nj01687d.

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5

Luchese, Cristiane, Ricardo Brandão, Carmine I. Acker, and Cristina W. Nogueira. "2,2′-Dipyridyl diselenide is a better antioxidant than other disubstituted diaryl diselenides." Molecular and Cellular Biochemistry 367, no. 1-2 (April 29, 2012): 153–63. http://dx.doi.org/10.1007/s11010-012-1328-5.

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6

Zhou, Long-Hu, and Yong-Min Zhang. "Low-valent Titanium Induced Reductive Coupling of Diaryl Diselenides with Acid Chlorides or Acid Anhydrides: Facile Synthesis of Selenoesters." Journal of Chemical Research 23, no. 1 (January 1999): 28–29. http://dx.doi.org/10.1177/174751989902300120.

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7

Balaguez, Renata A., Vanessa G. Ricordi, Rodrigo C. Duarte, Josene M. Toldo, Cristtofer M. Santos, Paulo H. Schneider, Paulo F. B. Gonçalves, Fabiano S. Rodembusch, and Diego Alves. "Bis-arylsulfenyl- and bis-arylselanyl-benzo-2,1,3-thiadiazoles: synthesis and photophysical characterization." RSC Advances 6, no. 55 (2016): 49613–24. http://dx.doi.org/10.1039/c6ra04157d.

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Анотація:

Bis-arylsulfenyl- and bis-arylselanyl-benzo-2,1,3-thiadiazoles were synthesized in good yields by copper-catalysed cross-coupling reaction of arylthiols or diaryl diselenides with the commercially available 4,7-dibromobenzo[c][1,2,5]thiadiazole.

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8

Kumar, R. Uday, Kommula Dileep, K. Harsha Vardhan Reddy, and Y. V. D. Nageswar. "Cu(OAc)2-Promoted Thiolation and Selenylation of C(sp2)-H Bonds Using a 2-Amino Oxazole Directing Group." Letters in Organic Chemistry 16, no. 2 (January 9, 2019): 110–16. http://dx.doi.org/10.2174/1570178615666180627111437.

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Анотація:

Cu-catalyzed thiolation or selenylation of aryl C-H bonds with diaryl disulfides and diphenyl diselenides was accomplished using a readily removable directing group. This protocol represents a convenient route for the formation of valuable diaryl sulfides or diphenyl selenides. This simple method gives a variety of functionalized diphenyl sulfides or diphenyl selenides in moderate to good yields in a simple and efficient way.

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9

Butov, G. M., V. M. Mokhov, Yu P. Tsapkova, R. L. Antipin, A. Yu Gavrilova, and N. V. Zyk. "Reaction of [3.3.1]propellanes with diaryl diselenides." Russian Journal of Organic Chemistry 46, no. 6 (June 2010): 929–30. http://dx.doi.org/10.1134/s1070428010060266.

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10

Oilunkaniemi, Raija, Risto S. Laitinen, and Markku Ahlgrén. "The Solid State Conformation of Diaryl Ditellurides and Diselenides: The Crystal and Molecular Structures of (C4H3E2)2E'2 (E = O, S; E' = Te, Se)." Zeitschrift für Naturforschung B 55, no. 5 (May 1, 2000): 361–68. http://dx.doi.org/10.1515/znb-2000-0503.

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Анотація:

The crystal and molecular structures of dithienyl ditelluride (C4H3S)2Te2 (1), difuryl ditelluride (C4H3O)2Te2 (2), dithienyl diselenide (C4H3S)2Se2 (3), and difuryl diselenide (C4H3O)2Se2 (4) are reported in this paper and compared to those of other simple diaryl ditellurides and diselenides. The chalcogen-chajcogen bonds exhibit approximately single bond lengths [Te-Te = 2.7337(8) and 2.7240(4) Å in 1 and 2, respectively; Se-Se = 2.357(1) and 2.368(2) Å in 3 and 4, respectively], as do the chalcogen-carbon bond lengths [Te-C = 2.095(9) - 2.104(6) in 1 and 2.091(6) - 2.105(9) Å in 2; Se-C = 1.87(1) - 1.90(1) Å in 3 and 1.887(8) - 1.897(10) Å in 4]. The aromatic rings are disordered. The dihedral angles C-E-E-C range from 79(2) to 96(1)° are consistent with the concept of minimized p lone-pair repulsion of adjacent chalcogen atoms. The dependence of molecular parameters on the angle between the aromatic rings and the chalcogen-chalcogen bonds follow trends established previously for aromatic disulfides. Though the bond parameters and conformations of 1 - 4 are similar, the packing of the molecules is different. The two ditellurides 1 and 2 show short Te···Te contacts (3.900 - 4.002 Å in 1 and 4.060 - 4.172 Å in 2). The two diselenides 3 and 4 do not exhibit close chalcogen-chalcogen interactions. The NMR spectroscopic properties of 1 - 4 are discussed.

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11

He, Wei-Bao, Luo-Lin Tang, Jun Jiang, Xiao Li, Xinhua Xu, Tian-Bao Yang, and Wei-Min He. "Paired Electrolysis Enabled Cyanation of Diaryl Diselenides with KSCN Leading to Aryl Selenocyanates." Molecules 28, no. 3 (February 1, 2023): 1397. http://dx.doi.org/10.3390/molecules28031397.

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Анотація:

The first example of paired electrolysis-enabled cyanation of diaryl diselenides, with KSCN as the green cyanating agent, has been developed. A broad range of aryl selenocyanates can be efficiently synthesized under chemical-oxidant- and additive-free, energy-saving and mild conditions.

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12

Saravanan, Perumal, and Pazhamalai Anbarasan. "Trifluoromethylthiolative 1,2-difunctionalization of alkenes with diselenides and AgSCF3." Chemical Communications 55, no. 32 (2019): 4639–42. http://dx.doi.org/10.1039/c9cc00815b.

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An efficient regioselective difunctionalization of alkenes via trifluoromethylthiolation has been accomplished employing diaryl diselenide and AgSCF₃ in the presence of BF₃·OEt₂.

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13

Taniguchi, Toshihide, Akinori Murata, Motonori Takeda, Takumi Mizuno, Akihiro Nomoto, and Akiya Ogawa. "Atom-Economical Synthesis of Unsymmetrical Diaryl Selenides from Arylhydrazines and Diaryl Diselenides." European Journal of Organic Chemistry 2017, no. 33 (September 5, 2017): 4928–34. http://dx.doi.org/10.1002/ejoc.201700938.

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14

Perin, G., M. B. Silveira, A. M. Barcellos, R. G. Jacob, and D. Alves. "Polyethylene glycol-400/H3PO2: an eco-friendly reductive system for the synthesis of selanylesters." Organic Chemistry Frontiers 2, no. 11 (2015): 1531–35. http://dx.doi.org/10.1039/c5qo00256g.

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Анотація:

An alternative green method was described for the synthesis of selanylesters by reactions of acyl chlorides with arylselenols, generated in situ by reaction of diaryl diselenides with hypophosphorous acid (H₃PO₂) using polyethylene glycol-400 (PEG-400) as the solvent.

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15

Pacuła, Agata J., Magdalena Obieziurska, Jacek Ścianowski, Katarzyna B. Kaczor, and Jędrzej Antosiewicz. "Water-dependent synthesis of biologically active diaryl diselenides." Arkivoc 2018, no. 3 (February 18, 2018): 153–64. http://dx.doi.org/10.24820/ark.5550190.p010.311.

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16

Bhowmick, Debasish, and Govindasamy Mugesh. "Introduction of a catalytic triad increases the glutathione peroxidase-like activity of diaryl diselenides." Organic & Biomolecular Chemistry 13, no. 34 (2015): 9072–82. http://dx.doi.org/10.1039/c5ob01294e.

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17

Zhao, Ruonan, Chenyu Yan, Yuanyuan Jiang, and Mingzhong Cai. "Efficient Heterogeneous Copper-Catalysed C–Se Coupling of Aryl Iodides with Symmetrical Diselenides towards Unsymmetrical Monoselenides." Journal of Chemical Research 42, no. 11 (November 2018): 584–88. http://dx.doi.org/10.3184/174751918x15409874473285.

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Анотація:

A highly efficient heterogeneous copper(I)-catalysed C–Se coupling of aryl iodides with diaryl diselenides was achieved in dimethylformamide at 110 °C under neutral conditions by using a 10 mol% of bipyridine-functionalised MCM-41-supported copper(I) complex [bpy-MCM-41-CuI] as the catalyst and magnesium as the reductive reagent, yielding a variety of unsymmetrical diaryl selenides in good to excellent yields. This heterogeneous copper catalyst can be easily recovered by a simple filtration of the reaction solution and recycled at least seven times without significant loss of activity.

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18

Ogawa, Akiya, Noriaki Takami, Masahito Sekiguchi, Hiroshi Yokoyama, Hitoshi Kuniyasu, Ilhyong Ryu, and Noboru Sonoda. "A Novel Thermal Addition of Diaryl Diselenides to Acetylenes." Chemistry Letters 20, no. 12 (December 1991): 2241–42. http://dx.doi.org/10.1246/cl.1991.2241.

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19

Giurg, Mirosław, and Ludwik Syper. "Diaryl Diselenides and Related Compounds as Oxygen-Transfer Agents." Phosphorus, Sulfur, and Silicon and the Related Elements 183, no. 4 (April 1, 2008): 970–85. http://dx.doi.org/10.1080/10426500801900956.

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20

Borges, V. C., L. Savegnago, G. Dadalt, and Cristina Wayne Nogueira. "Disubstituted Diaryl Diselenides Inhibit [3H]-Serotonin Uptake in Rats." Neurotoxicity Research 15, no. 1 (January 2009): 57–61. http://dx.doi.org/10.1007/s12640-009-9005-5.

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21

Butov, G. M., V. M. Mokhov, Yu P. Tsapkova, R. L. Antipin, A. Yu Gavrilova, and N. V. Zyk. "ChemInform Abstract: Reaction of [3.3.1]Propellanes with Diaryl Diselenides." ChemInform 41, no. 49 (November 11, 2010): no. http://dx.doi.org/10.1002/chin.201049174.

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22

Yasuike, Shuji, Mio Matsumura, Kohki Shibata, Sota Ozeki, Mizuki Yamada, Yuki Murata, and Naoki Kakusawa. "Synthesis of Unsymmetrical Diaryl Selenides: Copper-Catalyzed Se-Arylation of Diaryl Diselenides with Triarylbismuthanes." Synthesis 48, no. 05 (December 29, 2015): 730–36. http://dx.doi.org/10.1055/s-0035-1561280.

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23

Lee, Sun-Hee, Saet-Byeul Kim, and Myung-Sook Park. "One-Pot Synthetic Method of Symmetrical Diaryl Diselenides Using Na2Se2." Journal of the Korean Chemical Society 55, no. 3 (June 20, 2011): 546–49. http://dx.doi.org/10.5012/jkcs.2011.55.3.546.

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24

Li, Y., H. Wang, X. Li, T. Chen, and D. Zhao. "Coupling of Aryl Halides and Diaryl Diselenides with CuS/Fe." Synfacts 2011, no. 01 (December 21, 2010): 0106. http://dx.doi.org/10.1055/s-0030-1259133.

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25

Li, Y., H. Wang, X. Li, T. Chen, and D. Zhao. "Coupling of Aryl Halides and Diaryl Diselenides with CuS/Fe." Synfacts 2011, no. 03 (February 16, 2011): 0348. http://dx.doi.org/10.1055/s-0030-1259577.

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26

Goldani, Bruna, Vanessa G. Ricordi, Natália Seus, Eder J. Lenardão, Ricardo F. Schumacher, and Diego Alves. "Silver-Catalyzed Synthesis of Diaryl Selenides by Reaction of Diaryl Diselenides with Aryl Boronic Acids." Journal of Organic Chemistry 81, no. 22 (October 18, 2016): 11472–76. http://dx.doi.org/10.1021/acs.joc.6b02108.

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27

Młochowski, Jacek, Monika Brząszcz, Magdalena Chojnacka, Mirosław Giurg, and Halina Wójtowicz. "Diaryl diselenides and benzisoselenazol-3(2H)-ones as oxygen-transfer agents." Arkivoc 2004, no. 3 (April 23, 2004): 226–48. http://dx.doi.org/10.3998/ark.5550190.0005.319.

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28

Hung, Vu Thai, Cong Chi Tran, Yuki Yamamoto, Shintaro Kodama, Akihiro Nomoto, and Akiya Ogawa. "Clarification on the Reactivity of Diaryl Diselenides toward Hexacyclohexyldilead under Light." Molecules 26, no. 20 (October 16, 2021): 6265. http://dx.doi.org/10.3390/molecules26206265.

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Анотація:

In this study, the reactivity of organochalcogen compounds toward a representative alkyl-lead bond compound under light was investigated in detail. Under light irradiation, the Cy-Pb bond of Cy6Pb2 (Cy = cyclohexyl) undergoes homolytic cleavage to generate a cyclohexyl radical (Cy•). This radical can be successfully captured by diphenyl diselenide, which exhibits excellent carbon-radical-capturing ability. In the case of (PhS)2 and (PhTe)2, the yields of the corresponding cyclohexyl sulfides and tellurides were lower than that of (PhSe)2. This probably occurred due to the low carbon-radical-capturing ability of (PhS)2 and the high photosensitivity of the cyclohexyl-tellurium bond.

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29

Mugesh, G., Arunashree Panda, Harkesh B. Singh, Narayan S. Punekar, and Ray J. Butcher. "Glutathione Peroxidase-like Antioxidant Activity of Diaryl Diselenides: A Mechanistic Study." Journal of the American Chemical Society 123, no. 5 (February 2001): 839–50. http://dx.doi.org/10.1021/ja994467p.

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30

Pires, Camila S., Daniela H. de Oliveira, Maria R. B. Pontel, Jean C. Kazmierczak, Roberta Cargnelutti, Diego Alves, Raquel G. Jacob, and Ricardo F. Schumacher. "Molecular iodine-catalyzed one-pot multicomponent synthesis of 5-amino-4-(arylselanyl)-1H-pyrazoles." Beilstein Journal of Organic Chemistry 14 (November 6, 2018): 2789–98. http://dx.doi.org/10.3762/bjoc.14.256.

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A one-pot iodine-catalyzed multicomponent reaction has been developed for the selective preparation of 5-amino-4-(arylselanyl)-1H-pyrazoles from a diverse array of benzoylacetonitriles, arylhydrazines and diaryl diselenides. The reactions were conducted in MeCN as solvent at reflux temperature under air. The methodology presents a large functional group tolerance to electron-deficient, electron-rich, and bulky substituents and gave the expected products in good to excellent yields. The synthesized 1,3-diphenyl-4-(phenylselanyl)-1H-pyrazol-5-amine was submitted to an oxidative dehydrogenative coupling to produce a diazo compound confirmed by X-ray analysis.

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31

Nedel, Fernanda, Vinicius F. Campos, Diego Alves, Alan J. A. McBride, Odir A. Dellagostin, Tiago Collares, Lucielli Savegnago, and Fabiana K. Seixas. "Substituted diaryl diselenides: Cytotoxic and apoptotic effect in human colon adenocarcinoma cells." Life Sciences 91, no. 9-10 (September 2012): 345–52. http://dx.doi.org/10.1016/j.lfs.2012.07.023.

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32

Guo, Tao. "Ammonium iodide-mediated regioselective chalcogenation of chromones with diaryl disulfides and diselenides." Synthetic Communications 47, no. 22 (October 16, 2017): 2053–61. http://dx.doi.org/10.1080/00397911.2017.1364766.

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33

Kommula, Dileep, Qing Li, Siyang Ning, Wujun Liu, Qian Wang, and Zongbao K. Zhao. "Iodine mediated synthesis of diaryl diselenides using SeO2 as a selenium source." Synthetic Communications 50, no. 7 (February 21, 2020): 1026–34. http://dx.doi.org/10.1080/00397911.2020.1728775.

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34

Zhang, Songlin, та Fengshou Tian. "Zn/ZrCl4 System Induced Reductive Cleavage of the Se–Se Bond in Diaryl Diselenides: A Novel Method for the Synthesis of β-selenoesters and β-selenonitriles". Journal of Chemical Research 2001, № 5 (травень 2001): 198–99. http://dx.doi.org/10.3184/030823401103169496.

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Анотація:

The Se–Se bond in diselenides was reduced by Zn/ZrCl4 to produce selenolate anions, which react with α,β -unsaturated esters or α,β -unsaturated nitriles to afford β-selenoesters and β-selenonitriles, respectively.

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35

Zhang, Yongmin, Xueshun Jia, and Xunjun Zhou. "Samarium Diiodide-Induced Reduction of Amorphous Selenium: A Facile Synthesis of Diaryl Diselenides." Synthetic Communications 24, no. 9 (May 1994): 1247–52. http://dx.doi.org/10.1080/00397919408011724.

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36

Kuniyasu, Hitoshi, Akiya Ogawa, Shinichiro Miyazaki, Ilhyong Ryu, Nobuaki Kambe, and Noboru Sonoda. "Palladium-catalyzed addition and carbonylative addition of diaryl disulfides and diselenides to terminal acetylenes." Journal of the American Chemical Society 113, no. 26 (December 1991): 9796–803. http://dx.doi.org/10.1021/ja00026a013.

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37

Prigol, Marina, Cesar Augusto Bruning, Gilson Zeni, and Cristina W. Nogueira. "Protective effect of disubstituted diaryl diselenides on cerebral oxidative damage caused by sodium nitroprusside." Biochemical Engineering Journal 45, no. 2 (July 2009): 94–99. http://dx.doi.org/10.1016/j.bej.2009.02.015.

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38

Straliotto, Marcos Raniel, Jade de Oliveira, Gianni Mancini, Afonso C. D. Bainy, Alexandra Latini, Anna Maria Deobald, João B. T. Rocha, and Andreza Fabro de Bem. "Disubstituted diaryl diselenides as potential atheroprotective compounds: Involvement of TrxR and GPx-like systems." European Journal of Pharmaceutical Sciences 48, no. 4-5 (March 2013): 717–25. http://dx.doi.org/10.1016/j.ejps.2013.01.001.

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39

Saraiva, R. A., D. C. Bueno, P. A. Nogara та J. B. T. Rocha. "Molecular Docking Studies of Disubstituted Diaryl Diselenides as Mammalian δ-Aminolevulinic Acid Dehydratase Enzyme Inhibitors". Journal of Toxicology and Environmental Health, Part A 75, № 16-17 (серпень 2012): 1012–22. http://dx.doi.org/10.1080/15287394.2012.697810.

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40

Gonçalves, Loren C., Gabriela F. Fiss, Gelson Perin, Diego Alves, Raquel G. Jacob, and Eder J. Lenardão. "Glycerol as a promoting medium for cross-coupling reactions of diaryl diselenides with vinyl bromides." Tetrahedron Letters 51, no. 51 (December 2010): 6772–75. http://dx.doi.org/10.1016/j.tetlet.2010.10.107.

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41

ZHANG, Y., X. JIA, and X. ZHOU. "ChemInform Abstract: Samarium Diiodide-Induced Reduction of Amorphous Selenium: A Facile Synthesis of Diaryl Diselenides." ChemInform 25, no. 48 (August 18, 2010): no. http://dx.doi.org/10.1002/chin.199448197.

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42

Rui, Xiyan, Yueyue Zhu, Rupeng Dai, Chaoqun Huang, Chao Wang, Dongjuan Si, Xi Wang, et al. "An Efficient, Sustainable Rhodium‐Catalyzed and Ionic Liquid‐Mediated C−H Thiolation and Selenation of Acetanilide with Diaryl Disulfides and Diaryl Diselenides." Asian Journal of Organic Chemistry 10, no. 4 (March 24, 2021): 793–98. http://dx.doi.org/10.1002/ajoc.202100097.

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