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Journal articles on the topic 'C-C bonds'

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Published: 6 September 2023

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1

RITTER, STEPHEN K. "EXTREME C–C BONDS." Chemical & Engineering News 87, no. 19 (May 11, 2009): 32–33. http://dx.doi.org/10.1021/cen-v087n019.p032.

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2

Huntley, Deborah R., Georgios Markopoulos, Patrick M. Donovan, Lawrence T. Scott, and Roald Hoffmann. "Squeezing CC Bonds." Angewandte Chemie 117, no. 46 (November 25, 2005): 7721–25. http://dx.doi.org/10.1002/ange.200502721.

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3

Huntley, Deborah R., Georgios Markopoulos, Patrick M. Donovan, Lawrence T. Scott, and Roald Hoffmann. "Squeezing CC Bonds." Angewandte Chemie International Edition 44, no. 46 (November 25, 2005): 7549–53. http://dx.doi.org/10.1002/anie.200502721.

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4

Zeng, Xiaoming, and Xuefeng Cong. "Chromium-Catalyzed Cross-Coupling Reactions by Selective Activation of Chemically Inert Aromatic C–O, C–N, and C–H Bonds." Synlett 32, no. 13 (May 11, 2021): 1343–53. http://dx.doi.org/10.1055/a-1507-4153.

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AbstractTransition-metal-catalyzed cross-coupling has emerged as one of the most powerful and useful tools for the formation of C–C and C–heteroatom bonds. Given the shortage of resources of precious metals on Earth, the use of Earth-abundant metals as catalysts in developing cost-effective strategies for cross-coupling is a current trend in synthetic chemistry. Compared with the achievements made using first-row nickel, iron, cobalt, and even manganese catalysts, the group 6 metal chromium has rarely been used to promote cross-coupling. This perspective covers recent advances in chromium-catalyzed cross-coupling reactions in transformations of chemically inert C(aryl)–O, C(aryl)–N, and C(aryl)–H bonds, offering selective strategies for molecule construction. The ability of low-valent Cr with a high-spin state to participate in two-electron oxidative addition is highlighted; this is different from the mechanism involving single-electron transfer that is usually assigned to chromium-mediated transformations.1 Introduction2 Chromium-Catalyzed Kumada Coupling of Nonactivated C(aryl)–O and C(aryl)–N Bonds3 Chromium-Catalyzed Reductive Cross-Coupling of Two Nonactivated C(aryl)–Heteroatom Bonds4 Chromium-Catalyzed Functionalization of Nonactivated C(aryl)–H Bonds5 Conclusions and Outlook
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5

Egami, Hiromichi. "Fluorofunctionalizations of C–C Multiple Bonds and C–H Bonds." Chemical and Pharmaceutical Bulletin 68, no. 6 (June 1, 2020): 491–511. http://dx.doi.org/10.1248/cpb.c19-00856.

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6

Meng, Ge, Pengfei Li, Kai Chen, and Linghua Wang. "Recent Advances in Transition-Metal-Free Aryl C–B Bond Formation." Synthesis 49, no. 21 (September 26, 2017): 4719–30. http://dx.doi.org/10.1055/s-0036-1590913.

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Arylboronic acids and their derivatives are widely used in organic synthesis. Conventional methods for their preparation require either reactive organometallic reagents or transition-metal-mediated processes. In recent years, transition-metal-free reactions for aryl C–B bond formation that obviate preformed organometallic reagents have gained interest and have developed rapidly. These new reactions have shown significant advantages for the preparation of functionalized molecules. In this review, an overview of the recent advances in transition-metal-free aromatic borylation reactions is provided.1 Introduction2 Transition-Metal-Free Transformations of CAr–N Bonds to CAr–B Bonds3 Transition-Metal-Free Transformations of CAr–X Bonds to CAr–B Bonds4 Transition-Metal-Free Transformations of CAr–H Bonds to CAr–B Bonds5 Conclusion
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7

Luh, Tien-Yau. "Chelation Assisted Conversion of C-S Bonds into C-C Bonds." Phosphorus, Sulfur, and Silicon and the Related Elements 120, no. 1 (January 1, 1997): 259–73. http://dx.doi.org/10.1080/10426509708545523.

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8

Hamel, Jean-Denys, and Jean-François Paquin. "Activation of C–F bonds α to C–C multiple bonds." Chemical Communications 54, no. 73 (2018): 10224–39. http://dx.doi.org/10.1039/c8cc05108a.

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9

Kaupp, Gerd, and Jürgen Boy. "Overlong CC Single Bonds." Angewandte Chemie International Edition in English 36, no. 12 (February 3, 1997): 48–49. http://dx.doi.org/10.1002/anie.199700481.

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10

Wang, Chang-Sheng, Pierre H. Dixneuf, and Jean-François Soulé. "Photoredox Catalysis for Building C–C Bonds from C(sp2)–H Bonds." Chemical Reviews 118, no. 16 (July 16, 2018): 7532–85. http://dx.doi.org/10.1021/acs.chemrev.8b00077.

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11

LUH, T. Y. "ChemInform Abstract: Chelation-Assisted Conversion of C-S Bonds into C-C Bonds." ChemInform 29, no. 4 (June 24, 2010): no. http://dx.doi.org/10.1002/chin.199804268.

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12

Jia, C. "Efficient Activation of Aromatic C-H Bonds for Addition to C-C Multiple Bonds." Science 287, no. 5460 (March 17, 2000): 1992–95. http://dx.doi.org/10.1126/science.287.5460.1992.

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13

Del Bene, Janet E., Ibon Alkorta, and José Elguero. "Carbenes as Electron-Pair Donors To CO2 for C···C Tetrel Bonds and C–C Covalent Bonds." Journal of Physical Chemistry A 121, no. 20 (May 16, 2017): 4039–47. http://dx.doi.org/10.1021/acs.jpca.7b03405.

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14

Yeston, Jake. "Slicing through both C-C and C-H bonds." Science 357, no. 6353 (August 24, 2017): 768.17–770. http://dx.doi.org/10.1126/science.357.6353.768-q.

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15

Mori, A., M. Takahashi, K. Masui, H. Sekiguchi, N. Kobayashi, M. Funahashi, and N. Tamaoki. "Activating C-H Bonds Over C-Br Bonds to Make Oligothiophenes." Synfacts 2006, no. 11 (November 2006): 1115. http://dx.doi.org/10.1055/s-2006-949468.

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16

Nziko, Vincent de Paul N., and Steve Scheiner. "S···π Chalcogen Bonds between SF2or SF4and C–C Multiple Bonds." Journal of Physical Chemistry A 119, no. 22 (May 22, 2015): 5889–97. http://dx.doi.org/10.1021/acs.jpca.5b03359.

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17

A. Adrio, Luis, and King Kuok (Mimi) Hii. "Palladium-Catalyzed Heterofunctionalization of C-H, C=C and C≡ C Bonds." Current Organic Chemistry 15, no. 18 (September 1, 2011): 3337–61. http://dx.doi.org/10.2174/138527211797248003.

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18

Allen, Gregory W., Robert S. Armstrong, Manuel J. Aroney, Raymond K. Pierens, and Alan J. Williams. "Polarisability anisotropies of C—H, C—C, C—Cl and C—Br bonds." J. Chem. Soc., Faraday Trans. 2 84, no. 11 (1988): 1775–78. http://dx.doi.org/10.1039/f29888401775.

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19

Fukumoto, Yoshiya. "Catalytic Hydroamination of C-C Multiple Bonds." Journal of Synthetic Organic Chemistry, Japan 67, no. 7 (2009): 735–50. http://dx.doi.org/10.5059/yukigoseikyokaishi.67.735.

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20

RITTER, STEPHEN K. "WIDENING THE ROAD FOR C-C BONDS." Chemical & Engineering News 80, no. 5 (February 4, 2002): 26. http://dx.doi.org/10.1021/cen-v080n005.p026.

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21

Martínez-Guajardo, Gerardo, Kelling J. Donald, Bernard K. Wittmaack, Miguel Angel Vazquez, and Gabriel Merino. "Shorter Still: Compressing C−C Single Bonds." Organic Letters 12, no. 18 (September 17, 2010): 4058–61. http://dx.doi.org/10.1021/ol101671m.

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22

Martínez-Guajardo, Gerardo, Kelling J. Donald, Bernard K. Wittmaack, Miguel Angel Vazquez, and Gabriel Merino. "Shorter Still: Compressing C−C Single Bonds." Organic Letters 13, no. 1 (January 7, 2011): 172. http://dx.doi.org/10.1021/ol102654b.

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23

Suzuki, Takanori, Takashi Takeda, Hidetoshi Kawai, and Kenshu Fujiwara. "Ultralong C-C bonds in hexaphenylethane derivatives." Pure and Applied Chemistry 80, no. 3 (January 1, 2008): 547–53. http://dx.doi.org/10.1351/pac200880030547.

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The longer C-C bond than the standard (1.54 Å) is so weakened that it is cleaved easily, as found in the parent hexaphenylethane (HPE). However, the compounds with an ultralong C-C bond (1.75 Å) can be isolated as stable solids when the bond-dissociated species does not undergo any reactions other than bond reformation. This is the central point in designing the highly strained HPEs, which were obtained by two-electron reduction of the corresponding dications. Steric repulsion of "front strain" is the major factor to expand the central C-C bond of HPEs. During the detailed examination of the ultralong C-C bond, the authors discovered the intriguing phenomenon of "expandability": the C-C bond length can be altered over a wide range by applying only a small amount of energy (1 kcal mol-1) supplied by crystal packing force. This observation indicates that the much longer C-C bond than the shortest nonbonded contact (1.80 Å) will be realized under the rational molecular design concept.
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24

KAUPP, G., and J. BOY. "ChemInform Abstract: Overlong C-C Single Bonds." ChemInform 28, no. 16 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199716288.

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25

del Río, M. Pilar, José A. López, Miguel A. Ciriano, and Cristina Tejel. "Connecting CC Bonds to Tetrairidium Chains." Chemistry - A European Journal 19, no. 15 (February 28, 2013): 4707–11. http://dx.doi.org/10.1002/chem.201203769.

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26

Madasu, Jayashree, Shital Shinde, Rudradip Das, Sagarkumar Patel, and Amit Shard. "Potassium tert-butoxide mediated C–C, C–N, C–O and C–S bond forming reactions." Organic & Biomolecular Chemistry 18, no. 41 (2020): 8346–65. http://dx.doi.org/10.1039/d0ob01382j.

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27

Wang, Min, Xiang-Kui Gu, Hai-Yan Su, Jian-Min Lu, Ji-Ping Ma, Miao Yu, Zhe Zhang, and Feng Wang. "Preferential cleavage of C C bonds over C N bonds at interfacial CuO Cu2O sites." Journal of Catalysis 330 (October 2015): 458–64. http://dx.doi.org/10.1016/j.jcat.2015.08.001.

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28

Wang, Congyang, and Ting Liu. "Manganese-Catalyzed C(sp2)–H Addition to Polar Unsaturated Bonds." Synlett 32, no. 13 (March 27, 2021): 1323–29. http://dx.doi.org/10.1055/a-1468-6136.

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AbstractTransition-metal-catalyzed nucleophilic C–H addition of hydrocarbons to polar unsaturated bonds could intrinsically avoid prefunctionalization of substrates and formation of waste byproducts, thus featuring high step- and atom-economy. As the third most abundant transition metal, manganese-catalyzed C–H addition to polar unsaturated bonds remains challenging, partially due to the difficulty in building a closed catalytic cycle of manganese. In the past few years, we have developed manganese catalysis to enable the sp2-hydrid C–H addition to polar unsaturated bonds (e.g., imines, aldehydes, nitriles), which will be discussed in this personal account.1 Introduction2 Mn-Catalyzed N-Directed C(sp2)–H Addition to Polar Unsaturated Bonds3 Mn-Catalyzed O-Directed C(sp2)–H Addition to Polar Unsaturated Bonds4 Conclusion
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29

Rowland, Alex T. "C-H and C-D Bonds: An Experimental Approach to the Identity of C-H Bonds by Their Conversion to C-D Bonds." Journal of Chemical Education 80, no. 3 (March 2003): 311. http://dx.doi.org/10.1021/ed080p311.

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30

Chumakova, Natalia A., and Anatoly L. Buchachenko. "Spin propagation through the C–C and C–H bonds." Mendeleev Communications 25, no. 4 (July 2015): 264–66. http://dx.doi.org/10.1016/j.mencom.2015.07.010.

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31

PETKEWICH, RACHEL. "BREAKING C–F BONDS." Chemical & Engineering News 86, no. 35 (September 2008): 13. http://dx.doi.org/10.1021/cen-v086n035.p013.

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32

Chong, Eugene, and Suzanne A. Blum. "Aminoboration: Addition of B–N σ Bonds across C–C π Bonds." Journal of the American Chemical Society 137, no. 32 (August 10, 2015): 10144–47. http://dx.doi.org/10.1021/jacs.5b06678.

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33

Yang, Jia, Jing Xiao, Tieqiao Chen, Shuang-Feng Yin, and Li-Biao Han. "Efficient nickel-catalyzed phosphinylation of C–S bonds forming C–P bonds." Chemical Communications 52, no. 82 (2016): 12233–36. http://dx.doi.org/10.1039/c6cc06048j.

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The first nickel-catalyzed phosphinylation of C–S bonds forming C–P bonds is developed. The reaction can proceed readily with the simple Ni(cod)2 at a loading down to 0.1 mol% at the 10 mmol scale. Various aryl sulfur compounds, i.e. sulfides, sulfoxides and sulfones all couple with P(O)–H compounds to produce the corresponding organophosphorus compounds, which provides an efficient new method for the construction of C–P bonds.
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34

Chen, Zhen, Meng-Yu Rong, Jing Nie, Xue-Feng Zhu, Bing-Feng Shi, and Jun-An Ma. "Catalytic alkylation of unactivated C(sp3)–H bonds for C(sp3)–C(sp3) bond formation." Chemical Society Reviews 48, no. 18 (2019): 4921–42. http://dx.doi.org/10.1039/c9cs00086k.

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35

Mi, Zhiyuan, Jiahao Tang, Zhipeng Guan, Wei Shi, and Hao Chen. "Cleavage of C-C and C-O Bonds to Form C-C Bonds: Direct Cross-Coupling between Acetylenic Alcohols and Benzylic Carbonates." European Journal of Organic Chemistry 2018, no. 32 (August 17, 2018): 4479–82. http://dx.doi.org/10.1002/ejoc.201800861.

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36

Zhang, Honglin, Changduo Pan, Ning Jin, Zhangxi Gu, Hongwen Hu, and Chengjian Zhu. "Metal-free cascade construction of C–C bonds by activation of inert C(sp3)–H bonds." Chemical Communications 51, no. 7 (2015): 1320–22. http://dx.doi.org/10.1039/c4cc08629e.

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37

Terao, Jun, Misaki Nakamura, and Nobuaki Kambe. "Non-catalytic conversion of C–F bonds of benzotrifluorides to C–C bonds using organoaluminium reagents." Chemical Communications, no. 40 (2009): 6011. http://dx.doi.org/10.1039/b915620h.

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38

Jia, C., D. Piao, J. Oyamada, W. Lu, T. Kitamura, and Y. Fujiwara. "ChemInform Abstract: Efficient Activation of Aromatic C-H Bonds for Addition to C-C Multiple Bonds." ChemInform 31, no. 48 (November 28, 2000): no. http://dx.doi.org/10.1002/chin.200048266.

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39

Zhao, Yating, and Wujiong Xia. "Photochemical C–H bond coupling for (hetero)aryl C(sp2)–C(sp3) bond construction." Organic & Biomolecular Chemistry 17, no. 20 (2019): 4951–63. http://dx.doi.org/10.1039/c9ob00244h.

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This review highlights the recent advances in photochemical (hetero)aryl C(sp2)–C(sp3) bond construction via C–H bond coupling such as (hetero)arylation of C(sp3)–H bonds and alkylation of (hetero)aryl C(sp2)–H bonds.
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40

Li, Shuai-Shuai, Liu Qin, and Lin Dong. "Rhodium-catalyzed C–C coupling reactions via double C–H activation." Organic & Biomolecular Chemistry 14, no. 20 (2016): 4554–70. http://dx.doi.org/10.1039/c6ob00209a.

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41

Borpatra, Paran J., Bhaskar Deka, Mohit L. Deb, and Pranjal K. Baruah. "Recent advances in intramolecular C–O/C–N/C–S bond formation via C–H functionalization." Organic Chemistry Frontiers 6, no. 20 (2019): 3445–89. http://dx.doi.org/10.1039/c9qo00863b.

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42

Kennemur, Jennifer L., Rajat Maji, Manuel J. Scharf, and Benjamin List. "Catalytic Asymmetric Hydroalkoxylation of C–C Multiple Bonds." Chemical Reviews 121, no. 24 (December 3, 2021): 14649–81. http://dx.doi.org/10.1021/acs.chemrev.1c00620.

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43

Padilla, Rosa, Verónica Salazar, Margarita Paneque, José G. Alvarado-Rodríguez, Joaquín Tamariz, Héctor Pacheco-Cuvas, and Florencia Vattier. "Mild Oxidation of C−C Bonds of Benzoiridacycles." Organometallics 29, no. 12 (June 28, 2010): 2835–38. http://dx.doi.org/10.1021/om100196h.

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44

Smaligo, Andrew J., and Ohyun Kwon. "Dealkenylative Thiylation of C(sp3)–C(sp2) Bonds." Organic Letters 21, no. 21 (October 2019): 8592–97. http://dx.doi.org/10.1021/acs.orglett.9b03186.

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45

Chan, Antony P. Y., and Alexey G. Sergeev. "Metal-mediated cleavage of unsaturated C-C bonds." Coordination Chemistry Reviews 413 (June 2020): 213213. http://dx.doi.org/10.1016/j.ccr.2020.213213.

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46

Walter, Marc D, and Matthias Tamm. "Breaking News: Tungsten Cleaves Aromatic CC Bonds." Angewandte Chemie International Edition 49, no. 19 (April 14, 2010): 3264–66. http://dx.doi.org/10.1002/anie.201001197.

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47

Bernard, Julie, Esta van Heerden, Isabel W. C. E. Arends, Diederik J. Opperman, and Frank Hollmann. "Chemoenzymatic Reduction of Conjugated CC Double Bonds." ChemCatChem 4, no. 2 (December 6, 2011): 196–99. http://dx.doi.org/10.1002/cctc.201100312.

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48

Widenhoefer, Ross A., and Xiaoqing Han. "Gold-Catalyzed Hydroamination of C–C Multiple Bonds." European Journal of Organic Chemistry 2006, no. 20 (October 2006): 4555–63. http://dx.doi.org/10.1002/ejoc.200600399.

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49

Tombo, Gerardo M Ramos, and Camille Ganter. "Nucleophilic Addition to CC Bonds, Part X." Helvetica Chimica Acta 85, no. 10 (October 2002): 3575–87. http://dx.doi.org/10.1002/1522-2675(200210)85:10<3575::aid-hlca3575>3.0.co;2-q.

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50

Rybtchinski, Boris, and David Milstein. "Metal Insertion into C−C Bonds in Solution." Angewandte Chemie International Edition 38, no. 7 (April 1, 1999): 870–83. http://dx.doi.org/10.1002/(sici)1521-3773(19990401)38:7<870::aid-anie870>3.0.co;2-3.

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