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Journal articles on the topic 'Sulfonyl radicals'

Author: Grafiati
Published: 4 June 2021
Last updated: 1 February 2022

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1

Griesser, Markus, Jean-Philippe R. Chauvin, and Derek A. Pratt. "The hydrogen atom transfer reactivity of sulfinic acids." Chemical Science 9, no. 36 (2018): 7218–29. http://dx.doi.org/10.1039/c8sc02400f.

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Sulfinic acids are characterized to be very good H-atom donors to each of alkyl and alkoxyl radicals. In order to participate in useful radical chain reactions, the sulfonyl radicals must undergo fast propagating reactions to avoid autoxidation, which is surprisingly rate-limited by the reaction of sulfonyl radicals with oxygen.
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2

Freeman, Fillmore, та Monica C. Keindl. "Sulfinyl, α-Sulfinyl, Sulfonyl, and α-Sulfonyl Radicals". Sulfur reports 4, № 7 (1985): 231–98. http://dx.doi.org/10.1080/01961778508082480.

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3

Gilmore, Kerry, Brian Gold, Ronald J. Clark, and Igor V. Alabugin. "Convenient Ambient Temperature Generation of Sulfonyl Radicals." Australian Journal of Chemistry 66, no. 3 (2013): 336. http://dx.doi.org/10.1071/ch12499.

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Presented herein is a novel method for the efficient, ambient temperature generation of sulfonyl radicals from aryl and alkyl sulfonylbromides upon autoxidation of triethylborane (Et3B). The resultant radicals were regioselectively trapped via addition to terminal alkynes, generating a secondary vinyl radical that selectively abstracts a Br atom from RSO2Br, yielding the (E)-bromo vinylsulfones. Sensitivity towards Lewis basic groups was observed, presumably due to the disruptive coordination to Et3B before atom-transfer.
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4

Wang, Hanghang, Pengcheng Lian, Yonggao Zheng, Jingjing Li та Xiaobing Wan. "Cross coupling of sulfonyl radicals with silver-based carbenes: a simple approach to β-carbonyl arylsulfones". Organic & Biomolecular Chemistry 18, № 11 (2020): 2163–69. http://dx.doi.org/10.1039/d0ob00091d.

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5

Montermini, Florian, Emmanuel Lacôte та Max Malacria. "Reactivity of β-LactamidoN-Sulfonyl Radicals". Organic Letters 6, № 6 (2004): 921–23. http://dx.doi.org/10.1021/ol0363725.

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6

Huang, Xiaoqiang, Shipeng Luo, Olaf Burghaus, Richard D. Webster, Klaus Harms, and Eric Meggers. "Combining the catalytic enantioselective reaction of visible-light-generated radicals with a by-product utilization system." Chemical Science 8, no. 10 (2017): 7126–31. http://dx.doi.org/10.1039/c7sc02621h.

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We report an unusual reaction design in which a chiral bis-cyclometalated rhodium(iii) complex enables the stereocontrolled chemistry of photo-generated carbon-centered radicals and at the same time catalyzes an enantioselective sulfonyl radical addition to an alkene.
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7

Mase, Nobuyuki, Yoshihiko Watanabe та Takeshi Toru. "Discrimination of diastereotopic sulfonyl oxygens by intramolecular hydrogen bonding: Stereoselective hydrogenation of α-sulfonyl radicals". Tetrahedron Letters 40, № 14 (1999): 2797–800. http://dx.doi.org/10.1016/s0040-4039(99)00297-x.

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8

García‐Domínguez, Andrés, Simona Müller, and Cristina Nevado. "Nickel‐Catalyzed Intermolecular Carbosulfonylation of Alkynes via Sulfonyl Radicals." Angewandte Chemie International Edition 56, no. 33 (2017): 9949–52. http://dx.doi.org/10.1002/anie.201704862.

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9

CULSHAW, P. N., and J. C. WALTON. "ChemInform Abstract: Generation of Sulfonyl Radicals from Sulfonate Esters." ChemInform 22, no. 7 (2010): no. http://dx.doi.org/10.1002/chin.199107089.

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10

García‐Domínguez, Andrés, Simona Müller, and Cristina Nevado. "Nickel‐Catalyzed Intermolecular Carbosulfonylation of Alkynes via Sulfonyl Radicals." Angewandte Chemie 129, no. 33 (2017): 10081–84. http://dx.doi.org/10.1002/ange.201704862.

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11

Guo, Wei, Kailiang Tao, Wen Tan, Mingming Zhao, Lvyin Zheng, and Xiaolin Fan. "Recent advances in photocatalytic C–S/P–S bond formation via the generation of sulfur centered radicals and functionalization." Organic Chemistry Frontiers 6, no. 12 (2019): 2048–66. http://dx.doi.org/10.1039/c8qo01353e.

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12

Papastergiou, A., S. Perontsis, P. Gritzapis, et al. "Evaluation of O-alkyl and aryl sulfonyl aromatic and heteroaromatic amidoximes as novel potent DNA photo-cleavers." Photochemical & Photobiological Sciences 15, no. 3 (2016): 351–60. http://dx.doi.org/10.1039/c5pp00439j.

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O-Alkyl and aryl p-pyridine sulfonyl amidoxime derivatives are effective novel DNA photo-cleavers, generating highly efficient sulfonyloxyl radicals, able to cause a high ratio of single to double strand nicks.
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13

Yeun-Min, Tsai, Ke Bor-Wen та Lin Chao-Hsiung. "The study of intramolecular free radical cyclizations of α-sulfonyl and α-sulfinyl radicals". Tetrahedron Letters 31, № 42 (1990): 6047–50. http://dx.doi.org/10.1016/s0040-4039(00)98025-0.

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14

Barton, Derek H. R., Joseph Cs Jaszberenyi, and Emmanouil A. Theodorakis. "The invention of radical reactions. Part XXIII new reactions: Nitrile and thiocyanate transfer to carbon radicals from sulfonyl cyanides and sulfonyl isothiocyanates." Tetrahedron 48, no. 13 (1992): 2613–26. http://dx.doi.org/10.1016/s0040-4020(01)88524-0.

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15

Mase, Nobuyuki, Yoshihiko Watanabe та Takeshi Toru. "ChemInform Abstract: Discrimination of Diastereotopic Sulfonyl Oxygens by Intramolecular Hydrogen Bonding: Stereoselective Hydrogenation of α-Sulfonyl Radicals." ChemInform 30, № 27 (2010): no. http://dx.doi.org/10.1002/chin.199927102.

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16

Chen, Yiding, Nicole McNamara, Oliver May, Thanigaimalai Pillaiyar, David C. Blakemore, and Steven V. Ley. "Photoredox Generation of Sulfonyl Radicals and Coupling with Electron Deficient Olefins." Organic Letters 22, no. 15 (2020): 5746–48. http://dx.doi.org/10.1021/acs.orglett.0c01730.

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17

Bertrand, Frédérique, Frédéric Le Guyader, Lucia Liguori та ін. "α-Scission of sulfonyl radicals: a versatile process for organic synthesis". Comptes Rendus de l'Académie des Sciences - Series IIC - Chemistry 4, № 7 (2001): 547–55. http://dx.doi.org/10.1016/s1387-1609(01)01270-1.

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18

Ke, Bor-Wen, Chao-Hsiung Lin та Yeun-Min Tsai. "Generation and intramolecular cyclization of α-sulfinyl and α-sulfonyl radicals". Tetrahedron 53, № 23 (1997): 7805–26. http://dx.doi.org/10.1016/s0040-4020(97)00472-9.

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19

Della, Ernest W., and Sean D. Graney. "Ring closure of 2-thia- and 2-sulfonyl-5-hexenyl radicals." Tetrahedron Letters 41, no. 41 (2000): 7987–90. http://dx.doi.org/10.1016/s0040-4039(00)01377-0.

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20

BARTON, D. H. R., J. CS JASZBERENYI, and E. A. THEODORAKIS. "ChemInform Abstract: The Invention of Radical Reactions. Part 23. New Reactions: Nitrile and Thiocyanate Transfer to Carbon Radicals from Sulfonyl Cyanides and Sulfonyl Isothiocyanates." ChemInform 23, no. 31 (2010): no. http://dx.doi.org/10.1002/chin.199231094.

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21

TSAI, Y. M., B. W. KE та C. H. LIN. "ChemInform Abstract: The Study of Intramolecular Free Radical Cyclizations of α- Sulfonyl and α-Sulfinyl Radicals." ChemInform 22, № 40 (2010): no. http://dx.doi.org/10.1002/chin.199140067.

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22

Chatgilialoglu, C., D. Griller, and M. Guerra. "Experimental and theoretical approaches to the optical absorption spectra of sulfonyl radicals." Journal of Physical Chemistry 91, no. 14 (1987): 3747–50. http://dx.doi.org/10.1021/j100298a007.

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23

Zhang, Hanmo, E. Ben Hay, Steven J. Geib та Dennis P. Curran. "Radical Cyclizations of Cyclic Ene Sulfonamides Occur with β-Elimination of Sulfonyl Radicals to Form Polycyclic Imines". Journal of the American Chemical Society 135, № 44 (2013): 16610–17. http://dx.doi.org/10.1021/ja408387d.

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24

Gu, Zheng-Yang, Jing-Hao Li, Shun-Yi Wang, and Shun-Jun Ji. "Cobalt(ii)-catalyzed bis-isocyanide insertion reactions with sulfonyl azides via nitrene radicals: chemoselective synthesis of sulfonylamidyl amide and 3-imine indole derivatives." Chem. Commun. 53, no. 81 (2017): 11173–76. http://dx.doi.org/10.1039/c7cc06531k.

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25

KE, B. W., C. H. LIN та Y. M. TSAI. "ChemInform Abstract: Generation and Intramolecular Cyclization of α-Sulfinyl and . alpha.-Sulfonyl Radicals." ChemInform 28, № 43 (2010): no. http://dx.doi.org/10.1002/chin.199743085.

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26

Bertrand, Frederique, Frederic Le Guyader, Lucia Liguori та ін. "ChemInform Abstract: α-Scission of Sulfonyl Radicals: A Versatile Process for Organic Synthesis". ChemInform 33, № 10 (2010): no. http://dx.doi.org/10.1002/chin.200210258.

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27

Bertrand, Michèle P. "RECENT PROGRESS IN THE USE OF SULFONYL RADICALS IN ORGANIC SYNTHESIS. A REVIEW." Organic Preparations and Procedures International 26, no. 3 (1994): 257–90. http://dx.doi.org/10.1080/00304949409458426.

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28

CULSHAW, P. N., and J. C. WALTON. "ChemInform Abstract: Sulfonate Esters as Sources of Sulfonyl Radicals; Ring Closure Reactions of Alk-4- and -5-enesulfonyl Radicals." ChemInform 22, no. 45 (2010): no. http://dx.doi.org/10.1002/chin.199145111.

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29

Sugimoto, Hideki, Shuichi Nakamura, Yoshihiko Watanabe та Takeshi Toru. "Enantioselective hydrogen atom transfer to α-sulfonyl radicals controlled by selective coordination of a chiral Lewis acid to an enantiotopic sulfonyl oxygen". Tetrahedron: Asymmetry 14, № 19 (2003): 3043–55. http://dx.doi.org/10.1016/s0957-4166(03)00531-7.

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30

Zhang, Hanmo, E. Ben Hay, Steven J. Geib та Dennis P. Curran. "ChemInform Abstract: Radical Cyclizations of Cyclic Ene Sulfonamides Occur with β-Elimination of Sulfonyl Radicals to Form Polycyclic Imines." ChemInform 45, № 19 (2014): no. http://dx.doi.org/10.1002/chin.201419097.

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31

Hofman, Kamil, Nai‐Wei Liu, and Georg Manolikakes. "Radicals and Sulfur Dioxide: A Versatile Combination for the Construction of Sulfonyl‐Containing Molecules." Chemistry – A European Journal 24, no. 46 (2018): 11852–63. http://dx.doi.org/10.1002/chem.201705470.

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32

Everett, Steven A., Madeleine F. Dennis, Kantilal B. Patel, Susan Maddix, Subhas C. Kundu, and Robin L. Willson. "Scavenging of Nitrogen Dioxide, Thiyl, and Sulfonyl Free Radicals by the Nutritional Antioxidant -Carotene." Journal of Biological Chemistry 271, no. 8 (1996): 3988–94. http://dx.doi.org/10.1074/jbc.271.8.3988.

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33

Razskazovskii, Yu V., M. V. Roginskaya, and M. Ya Mel'nikov. "Two Pathways of SO2 Addition to Carbon-Centered Free Radicals Grafted to a Silica Surface: Sulfonyl and Oxysulfinyl Radical Formation." Journal of Physical Chemistry 98, no. 46 (1994): 12003–7. http://dx.doi.org/10.1021/j100097a028.

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34

BERTRAND, M. P. "ChemInform Abstract: Recent Progress in the Use of Sulfonyl Radicals in Organic Synthesis. A Review." ChemInform 25, no. 47 (2010): no. http://dx.doi.org/10.1002/chin.199447304.

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35

Della, Ernest W., and Sean D. Graney. "Regioselectivity of Ring Closure of 2-Thia- and 2-Sulfonyl-5-methyl-5-hexenyl Radicals." Organic Letters 4, no. 23 (2002): 4065–67. http://dx.doi.org/10.1021/ol0267836.

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36

Schöneich, Christian, Uwe Dillinger, Franz von Bruchhausen, and Klaus-Dieter Asmus. "Oxidation of polyunsaturated fatty acids and lipids through thiyl and sulfonyl radicals: Reaction kinetics, and influence of oxygen and structure of thiyl radicals." Archives of Biochemistry and Biophysics 292, no. 2 (1992): 456–67. http://dx.doi.org/10.1016/0003-9861(92)90016-p.

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37

Chatgilialoglu, Chryssostomos, Olivier Mozziconacci, Maurizio Tamba, et al. "Kinetic Studies on the Formation of Sulfonyl Radicals and Their Addition to Carbon–Carbon Multiple Bonds." Journal of Physical Chemistry A 116, no. 29 (2012): 7623–28. http://dx.doi.org/10.1021/jp304863y.

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38

Zheng, Danqing, Jiyao Yu, and Jie Wu. "Generation of Sulfonyl Radicals from Aryldiazonium Tetrafluoroborates and Sulfur Dioxide: The Synthesis of 3-Sulfonated Coumarins." Angewandte Chemie 128, no. 39 (2016): 12104–8. http://dx.doi.org/10.1002/ange.201607292.

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39

Zheng, Danqing, Jiyao Yu, and Jie Wu. "Generation of Sulfonyl Radicals from Aryldiazonium Tetrafluoroborates and Sulfur Dioxide: The Synthesis of 3-Sulfonated Coumarins." Angewandte Chemie International Edition 55, no. 39 (2016): 11925–29. http://dx.doi.org/10.1002/anie.201607292.

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40

Ollivier, Cyril, and Philippe Renaud. "A Novel Approach for the Formation of Carbon−Nitrogen Bonds: Azidation of Alkyl Radicals with Sulfonyl Azides." Journal of the American Chemical Society 123, no. 20 (2001): 4717–27. http://dx.doi.org/10.1021/ja004129k.

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41

Jiang, Yang-Ye, Sen Liang, Cheng-Chu Zeng, Li-Ming Hu, and Bao-Guo Sun. "Electrochemically initiated formation of sulfonyl radicals: synthesis of oxindoles via difunctionalization of acrylamides mediated by bromide ion." Green Chemistry 18, no. 23 (2016): 6311–19. http://dx.doi.org/10.1039/c6gc01970f.

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42

da Silva Corrêa, Carlos M. M., M. Daniela C. M. Fleming, M. Augusta B. C. S. Oliveira, and Ermelinda M. J. Garrido. "The importance of polar, resonance, steric and solvent effects in the addition of sulfonyl radicals to alkenes." J. Chem. Soc., Perkin Trans. 2, no. 9 (1994): 1993–2000. http://dx.doi.org/10.1039/p29940001993.

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43

Naghipur, Ali, Krzysztof Reszka, J. William Lown, and Anne-Marie Sapse. "Benzoxathiete and related structures: experimental and quantum chemical studies." Canadian Journal of Chemistry 68, no. 11 (1990): 1950–60. http://dx.doi.org/10.1139/v90-300.

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The products, plausible intermediates, and their mechanisms of formation in the aprotic diazotization of 2-[(2-acetoxyethyl)-sulfinyl (and sulfonyl)]anilines with isoamyl nitrate have been investigated by experimental and quantum chemical methods. Oxidation of 1,2,3-benzthiadiazole with hydrogen peroxide in acetic acid affords 1,2,3-benzthiadiazole-1-oxide, 13. The thermal stability of 13 up to 135 °C, together with EPR evidence which disfavors an aryldiazenyl radical precursor, discount 13 as an intermediate in the formation of benzoxathiete 14 or its valence tautomer 17 during aprotic diazot
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44

Nguyen, Thi Ngoc, Thi Phuong Thuy Tran, Thi Hoang Mai Vu, et al. "6-Nitro-7-tosylquinazolin-4(3H)-one." Molbank 2020, no. 4 (2020): M1168. http://dx.doi.org/10.3390/m1168.

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Sulfones are important building blocks in the construction of biologically active molecules or functional materials. The sulfonyl functional group in sulfones is so versatile that it can act as either a nucleophile, an electrophile, or a radical in different organic reactions. Recently, quinazoline sulfones have been used to build asymmetrical ether derivatives as inhibitors of signaling pathways governed by tyrosine kinases and the epidermal growth factor-receptor. In this paper, we report a facile synthesis of a novel quinazoline sulfone, 6-nitro-7-tosylquinazolin-4(3H)-one (III), using the
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45

Della, Ernest W., та Sean D. Graney. "The Regiochemistry of Cyclization of α-Sulfenyl-, α-Sulfinyl-, and α-Sulfonyl-5-hexenyl Radicals: Procedures Leading to Regioselective Syntheses of Cyclic Sulfones and Sulfoxides". Journal of Organic Chemistry 69, № 11 (2004): 3824–35. http://dx.doi.org/10.1021/jo0497306.

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46

Narasaka, Koichi, Takashi Mochizuki, and Satoshi Hayakawa. "Generation of Sulfonyl Radicals from Sodium Sulfinates by Oxidation with Metallic Oxidants and Their Addition Reaction with Olefins." Chemistry Letters 23, no. 9 (1994): 1705–8. http://dx.doi.org/10.1246/cl.1994.1705.

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47

Kameyama, Tomomi, and Akinori Takasu. "Electrophoretic Vinyl Polymers Prepared via Atom Transfer Radical Polymerization and Smart Coating on Metals." Key Engineering Materials 654 (July 2015): 37–41. http://dx.doi.org/10.4028/www.scientific.net/kem.654.37.

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We found non-ionic polymer containing ester and sulfonyl group, poly (ester-sulfone), showed anode-selective electrophoresis under the electrophoretic deposition (EPD) condition. In this paper we investigated an electrophoretic behavior of vinyl porymer having sulfonyl group in the side chains and compared with the main chain type of poly (ester-sulfone). Herein, we synthesized new poly (methacrylate) containing pendent sulfone to investigate the electrophoretic behavior.
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48

Hwang, Jin-Woo, Sun Hee Cheong, Yon-Suk Kim, et al. "Effects of dietary supplementation of oriental herbal medicine residue and methyl sulfonyl methane on the growth performance and meat quality of ducks." Animal Production Science 57, no. 5 (2017): 948. http://dx.doi.org/10.1071/an15134.

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The present study was conducted to determine the effect of supplementation with oriental herbal medicine residue (OHMR) and methyl sulfonyl methane (MSM) on the growth performance and meat quality of ducks during a 42-day feeding period. In total, 270 Cherry Valley male ducklings were fed diets supplemented with 0.03% MSM alone (MSM group) and with a combination of 0.03% MSM and 0.5% OHMR (MSM–OHMR group). Supplementing the diet with a combination of OHMR and MSM resulted in a significant (P < 0.05) decrease in the mortality rate and serum total cholesterol concentration, and in an increase
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49

Nikishin, Gennady I., Emmanuil I. Troyansky та Margarita I. Lazareva. "Regioselective one-step γ-chlorination of alkanesulfonamides. Preponderance of 1,5-H migration from sulfonyl amide moiety in sulfonylamidyl radicals". Tetrahedron Letters 26, № 31 (1985): 3743–44. http://dx.doi.org/10.1016/s0040-4039(00)89238-2.

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50

DA SILVA CORREA, C. M. M., M. D. C. M. FLEMING, M. A. B. C. S. OLIVEIRA, and E. M. J. GARRIDO. "ChemInform Abstract: The Importance of Polar, Resonance, Steric and Solvent Effects in the Addition of Sulfonyl Radicals to Alkenes." ChemInform 26, no. 8 (2010): no. http://dx.doi.org/10.1002/chin.199508087.

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