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Journal articles on the topic 'Halogen exchange reactions'

Author: Grafiati

Published: 4 June 2021

Last updated: 11 February 2022

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1

Bonniface, David W., John D. Scott, Michael J. Watson, et al. "Halogen exchange reactions for CFC alternatives." Green Chemistry 1, no. 1 (1999): 9–11. http://dx.doi.org/10.1039/a808021f.

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2

Nakada, Masahiro, Sei-ichi Tokumoto, and Minoru Hirota. "Fe3O4-Catalyzed Halogen-Exchange Reactions of Polyhalomethanes." Bulletin of the Chemical Society of Japan 60, no. 11 (1987): 3979–83. http://dx.doi.org/10.1246/bcsj.60.3979.

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3

Fu, Weimin, Xingya Li, and Xikui Jiang. "Base initiated halogen-exchange reactions between perhaloalkanes." Science in China Series B: Chemistry 40, no. 5 (1997): 475–84. http://dx.doi.org/10.1007/bf02875415.

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4

Okamoto, Masaki, Hiroyuki Tsukada, Syun Fukasawa, and Aya Sakajiri. "Synthesis of hollow and rattle-type mesoporous silica spheres by treating layered mesoporous silica with a basic solution, and using the spheres as microreactors for two-phase reactions." Journal of Materials Chemistry A 3, no. 22 (2015): 11880–90. http://dx.doi.org/10.1039/c5ta01863c.

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5

Iddon, Brian, and Brian Iddon. "Metallation and Metal-halogen Exchange Reactions of Imidazoles." HETEROCYCLES 23, no. 2 (1985): 417. http://dx.doi.org/10.3987/r-1985-02-0417.

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6

Sheppard, Tom D. "Metal-catalysed halogen exchange reactions of aryl halides." Organic & Biomolecular Chemistry 7, no. 6 (2009): 1043. http://dx.doi.org/10.1039/b818155a.

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7

Bonnafoux, Laurence, Nathalie Nicod, Frederic Leroux, Berengere Quissac, and Francoise Colobert. "New Vistas in Halogen/Metal Exchange Reactions: The Discrimination Between Seemingly Equal Halogens." Letters in Organic Chemistry 3, no. 2 (2006): 165–69. http://dx.doi.org/10.2174/157017806775224279.

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8

Abe, Hajime, and Hitomi Suzuki. "Copper-Mediated Nucleophilic Displacement Reactions of 1-Haloalkynes. Halogen-Halogen Exchange and Sulfonylation." Bulletin of the Chemical Society of Japan 72, no. 4 (1999): 787–98. http://dx.doi.org/10.1246/bcsj.72.787.

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9

Geherty, Maryll, James Melnyk, Keith Chomsky та David A. Hunt. "Halogen–metal exchange reactions of bromoaryl-substituted β-lactams". Tetrahedron Letters 54, № 36 (2013): 4934–36. http://dx.doi.org/10.1016/j.tetlet.2013.07.007.

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10

Gast, Rainer, Thomas Kaukorat, Ion Neda, and Reinhard Schmutzler. "Das 2-Halogen-5,6-benzo-1,3,2-dioxaphosphorinan-4-on-Ringsystem / The 2-Halogeno-5,6-benzo-1,3,2-dioxaphosphorinan-4-one Ring System." Zeitschrift für Naturforschung B 48, no. 7 (1993): 867–74. http://dx.doi.org/10.1515/znb-1993-0703.

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The reaction of salicylic acid with phosphorus trichloride furnished the previously known 2-chloro-5,6-benzo-1,3,2-dioxaphosphorinan-4-one heterocycle 1 which was unambiguously characterized, for the first time, by NMR spectroscopy and mass spectrometry. The fluorine and bromine analogues of 1, 2 and 3 were synthesized from 1, using exchange reactions. The iodo derivative, 4, owing to its instability, could be identified only in the reaction mixture by 1H and 31P NMR spectroscopy. The amine derivatives 5-8 were obtained from 1 using standard exchange reactions, either with silylated amines or

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11

Music, Arif, and Dorian Didier. "Organocerium: A New Contender for Halogen–Metal Exchanges." Synlett 30, no. 16 (2019): 1843–49. http://dx.doi.org/10.1055/s-0037-1611843.

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In the context of our current research on dependable and sustainable methods for C–C bond-forming reactions, we have recently developed new strategies to generate organocerium reagents through simple bromide–cerium exchanges. n-Bu3Ce enabled a fast and general access to functionalized triaryl- and alkenyl cerium species from the corresponding aryl- and alkenyl bromides. A broad range of these new organocerium species was engaged in Zweifel’s olefination, allowing for the synthesis of widely substituted alkene derivatives in a stereospecific way. Herein, we place the formation of organocerium s

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12

Jedlicka, Brigitte, Robert H. Crabtree, and Per E. M. Siegbahn. "Origin of Solvent Acceleration in Organolithium Metal−Halogen Exchange Reactions." Organometallics 16, no. 26 (1997): 6021–23. http://dx.doi.org/10.1021/om9705721.

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13

Cooke, Jr., Manning, and Jian-Jie Huang. "Metal-Halogen Exchange-Initiated Cyclization Reactions of Dienes and Enynes." Synlett 1997, Sup. I (1997): 535–36. http://dx.doi.org/10.1055/s-1997-6133.

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14

Yeardley, Callum, Alan R. Kennedy, Philippe C. Gros, et al. "Structural and metal–halogen exchange reactivity studies of sodium magnesiate biphenolate complexes." Dalton Transactions 49, no. 16 (2020): 5257–63. http://dx.doi.org/10.1039/d0dt00904k.

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15

Abe, Hajime, and Hitomi Suzuki. "ChemInform Abstract: Copper-Mediated Nucleophilic Displacement Reactions of 1-Haloalkynes. Halogen-Halogen Exchange and Sulfonylation." ChemInform 30, no. 34 (2010): no. http://dx.doi.org/10.1002/chin.199934045.

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16

Cooke, Manning P., and Rexford K. Widener. "Lithium-halogen exchange-initiated cyclization reactions. 3. Intramolecular conjugate addition reactions of unsaturated acylphosphoranes." Journal of Organic Chemistry 52, no. 8 (1987): 1381–96. http://dx.doi.org/10.1021/jo00384a001.

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17

Atefi, Farzad, Oliver B. Locos, Mathias O. Senge, and Dennis P. Arnold. "meso-iodo- and meso-iodovinylporphyrins via organopalladium porphyrins and the crystal structure of 5-iodo-10,20-diphenylporphyrin." Journal of Porphyrins and Phthalocyanines 10, no. 03 (2006): 176–85. http://dx.doi.org/10.1142/s1088424606000211.

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The regiospecific halogen exchange reactions of various easily accessible meso-bromoporphyrins to obtain meso-iodoporphyrins, using η1-palladioporphyrins as intermediates, have been investigated. This one-pot methodology allows the isolation of meso-iodoporphyrins in excellent yields with short reaction times. Similarly meso-(2-bromoethenyl)porphyrins can be converted to their iodoethenyl analogues. These iodoporphyrins show great potential as starting materials for various palladium catalyzed reactions. The X-ray crystal structure of 5-iodo-10,20-diphenylporphyrin has been determined.

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18

Geherty, Maryll, James Melnyk, Keith Chomsky та David A. Hunt. "ChemInform Abstract: Halogen-Metal Exchange Reactions of Bromoaryl-Substituted β-Lactams." ChemInform 45, № 1 (2013): no. http://dx.doi.org/10.1002/chin.201401113.

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19

Shi, Lei, Yuanyuan Chu, Paul Knochel, and Herbert Mayr. "Leaving Group Dependence of the Rates of Halogen–Magnesium Exchange Reactions." Organic Letters 14, no. 10 (2012): 2602–5. http://dx.doi.org/10.1021/ol300906a.

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20

Uhlig, Wolfram. "Zur gezielten Synthese funktionell substituierter Oligosilane aus Silyltriflaten und Aminosilyllithiumverbindungen / Tailor-Made Synthesis of Functional Substituted Oligosilanes from Silyl Triflates and (Aminosilyl)Lithium Compounds." Zeitschrift für Naturforschung B 58, no. 1 (2003): 183–90. http://dx.doi.org/10.1515/znb-2003-0128.

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Abstract Diethylamino substituted silyllithium compounds have been prepared in situ from the corresponding phenylchlorosilanes and lithium. These reagents undergo coupling reactions with triflate derivatives of silanes and oligosilanes. Exchange processes analogous to metal halogen exchange and Si-Si bond cleavage, which are side reactions with chlorosilanes, were not observed. Based on the coupling reaction and the amino-to-triflate transformation, functionalized tri-, tetra-, penta- und hexasilanes have been synthesized. α,ω-Triflate substituted oligosilanes containing π-systems have also be

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21

Ando, Tsuyoshi, Masami Kamigaito, and Mitsuo Sawamoto. "Reversible Activation of Carbon−Halogen Bonds by RuCl2(PPh3)3: Halogen Exchange Reactions in Living Radical Polymerization1." Macromolecules 33, no. 8 (2000): 2819–24. http://dx.doi.org/10.1021/ma991989g.

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22

Manolikakes, Sophia M., Nadja M. Barl, Christoph Sämann, and Paul Knochel. "Review. Regioselective Functionalization of Pyridines using a Directed Metalation or a Halogen/Metal Exchange." Zeitschrift für Naturforschung B 68, no. 5-6 (2013): 411–22. http://dx.doi.org/10.5560/znb.2013-3061.

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This review describes the various ways of functionalizing the pyridine scaffold using either directed metalation or halogen/metal exchange. Deprotonation can be accomplished with different lithium amides or alkyllithium reagents at low temperature. Milder conditions and higher functional group tolerance can be achieved by using ate-bases with different metals (Cd, Mg, Zn) or TMP (2,2,6,6- tetramethylpiperidyl) metal reagents (metal=Mg, Zn, Zr). With alkyllithium reagents it is also possible, by carefully adjusting the reaction conditions, to perform bromine/lithium exchange reactions. Organoma

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23

Suresh, B. S., and D. K. Padma. "Halogen exchange reactions of silicon tetrafluoride with phosphorus trichloride and phosphoryl chloride." Journal of Fluorine Chemistry 29, no. 4 (1985): 463–66. http://dx.doi.org/10.1016/s0022-1139(00)85111-8.

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24

Kleščíková, Lucia, Jana Doháňošová, and Róbert Fischer. "4-Bromo-2,3-dihydroisoxazoles: synthesis and application in halogen-lithium exchange reactions." Tetrahedron 71, no. 36 (2015): 6112–15. http://dx.doi.org/10.1016/j.tet.2015.06.102.

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25

Nithyanandhan, Jayaraj, and Narayanaswamy Jayaraman. "Efficient halogen–lithium exchange reactions to functionalize poly(alkyl aryl ether) dendrimers." Tetrahedron 62, no. 26 (2006): 6228–35. http://dx.doi.org/10.1016/j.tet.2006.04.052.

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26

Guber, A., and U. Köhler. "Halogen exchange reactions of silicon tetrachloride with fluorine and fluorine-containing substances." Journal of Fluorine Chemistry 58, no. 2-3 (1992): 321. http://dx.doi.org/10.1016/s0022-1139(00)80784-8.

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27

Rozov, Leonid A., Ralph A. Lessor, Linas V. Kudzma, and Keith Ramig. "The fluoromethyl ether sevoflurane as a fluoride source in halogen-exchange reactions." Journal of Fluorine Chemistry 88, no. 1 (1998): 51–54. http://dx.doi.org/10.1016/s0022-1139(97)00135-8.

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28

Cooke, Manning P. "Metal-halogen exchange-initiated intramolecular conjugate addition reactions of conjugated acetylenic esters." Journal of Organic Chemistry 58, no. 24 (1993): 6833–37. http://dx.doi.org/10.1021/jo00076a053.

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29

Cooke, Manning P., and D. Gopal. "Tandem metal-halogen exchange-initiated conjugate addition reactions of conjugated acetylenic esters." Journal of Organic Chemistry 59, no. 1 (1994): 260–63. http://dx.doi.org/10.1021/jo00080a048.

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30

COOKE, M. P. JUN, and J. J. HUANG. "ChemInform Abstract: Metal-Halogen Exchange-Initiated Cyclization Reactions of Dienes and Enynes." ChemInform 28, no. 41 (2010): no. http://dx.doi.org/10.1002/chin.199741109.

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31

Balkenhohl, Moritz, Dorothée S. Ziegler, Alexandre Desaintjean, et al. "Preparation of Polyfunctional Arylzinc Organometallics in Toluene by Halogen/Zinc Exchange Reactions." Angewandte Chemie International Edition 58, no. 37 (2019): 12898–902. http://dx.doi.org/10.1002/anie.201906898.

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32

Blockhaus, Tobias, Stefanie Bernhartzeder, Werner Kempinger, Christian Klein‐Heßling, Stefan Weigand, and Karlheinz Sünkel. "Evidence for “Halogen‐Dance” and Ring‐Exchange Reactions in Chloro‐methylthio‐ferrocenes." European Journal of Organic Chemistry 2020, no. 42 (2020): 6576–87. http://dx.doi.org/10.1002/ejoc.202001032.

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33

Politanskaya, Larisa V., Pavel A. Fedyushin, Tatyana V. Rybalova, Artem S. Bogomyakov, Nargiz B. Asanbaeva, and Evgeny V. Tretyakov. "Fluorinated Organic Paramagnetic Building Blocks for Cross-Coupling Reactions." Molecules 25, no. 22 (2020): 5427. http://dx.doi.org/10.3390/molecules25225427.

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New stable polyfluorinated nitroxide radicals for use in cross-coupling reactions, namely, N-tert-butyl-N-oxyamino-2,3,5,6-tetrafluoro-4-iodobenzene and N-tert-butyl-N-oxyamino-2,3,5,6-tetrafluoro-4-ethynylbenzene, were prepared from perfluoroiodobenzene. The reaction of the polyfluoro derivative with tert-butylamine under autoclaving conditions leading to the formation of N-tert-butyl-2,3,5,6-tetrafluoro-4-iodoaniline proved to be the key stage of the whole process. The fluorinated tert-butyl iodophenyl nitroxide was found to form in a solid state via N–O···I halogen bonds, a one-dimensional

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34

Naeimi, H., and Z. S. Nazifi. "Uranyl Schiff base complexes as new heterogeneous catalysts for halogen exchange reactions between alkyl halides and elemental halogens." Russian Chemical Bulletin 64, no. 8 (2015): 1814–18. http://dx.doi.org/10.1007/s11172-015-1076-2.

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35

Einholz, Wolfgang, Walter Gollinger, and Wolfgang Haubold. "Ligandenaustauschreaktionen zwischen Halogenboranen und Alkylsilanen/Ligand Exchange Reactions between Haloboranes and Alkylsilanes." Zeitschrift für Naturforschung B 45, no. 1 (1990): 25–30. http://dx.doi.org/10.1515/znb-1990-0107.

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Abstract In a ligand exchange reaction between BHal3 (Hal = Cl, Br) and the tetraalkylsilanes Et4Si, (Me3Si)2CH2 or Ph2CHSiMe3 the alkylhaloboranes EtBBr2 or MeBHal2 and the alkylhalosilanes Et3SiBr, HalMe2Si-CH2-SiMe3, (HalMe2Si)2CH2, and Ph2CHSiMe2Br, respectively, are formed. Similarly, the methyloligosilanes (Me3Si)2 (1) and (Me3Si)2SiMe2 (2) react with BHal3 (Hal = Cl, Br, I) via methyl-halogen-transfer to give HalMe2Si-SiMe3 (Hal = Cl, Br, I), (HalMe2Si)2 (Hal = Br, I), HalMe2Si - SiMe2-SiMe3, (Me3Si)2SiMeHal, HalMe2Si - SiMeHal -SiMe3, (HalMe2Si)SiMe2 (Hal = Cl, Br) or (BrMe2Si)2SiMeBr

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36

Schmidt, Rüdiger, Peter Osswald, Martin Könemann, and Frank Würthner. "Synthetic Routes to Core-fluorinated Perylene Bisimide Dyes and their Properties." Zeitschrift für Naturforschung B 64, no. 6 (2009): 735–46. http://dx.doi.org/10.1515/znb-2009-0621.

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Numerous core-fluorinated perylene bisimide (PBI) dyes with various substituents at the imide positions have been synthesized by different methods. Core-difluorinated PBIs 4a-f are obtained by imidization of difluoro-substituted perylene bisanhydride 1 with appropriate primary amines or, alternatively, by nucleophilic halogen exchange reactions (Halex process) of the corresponding dibromosubstituted PBIs 2a-d,f with potassium fluoride. Core-tetrafluorinated PBIs 5a-c could also be synthesized by halogen exchange reactions of the respective tetrachlorinated PBIs 3a-c. In particular, core-fluori

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37

Ido, Tadaatsu, Takanobu Yamamoto, Gong Jin, and Shigeo Goto. "Third-phase catalytic activity of halogen exchange reactions in phase transfer catalytic system." Chemical Engineering Science 52, no. 20 (1997): 3511–20. http://dx.doi.org/10.1016/s0009-2509(97)00165-6.

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38

Comins, Daniel L., Jason M. Nolan, and Ibrahim D. Bori. "Regioselective lithium–halogen exchange and palladium-catalyzed cross-coupling reactions of 2,4-dihaloquinolines." Tetrahedron Letters 46, no. 39 (2005): 6697–99. http://dx.doi.org/10.1016/j.tetlet.2005.07.137.

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39

Orvik, Jon A. "Facile Halogen Exchange Reactions: Chloroform with Bromoform and Carbon Tetrachloride with Carbon Tetrabromide." Journal of Organic Chemistry 61, no. 15 (1996): 4933–36. http://dx.doi.org/10.1021/jo951692q.

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40

Cooke, Manning P. "Formation of polycyclic carbocycles through metal-halogen exchange-initiated intramolecular conjugate addition reactions." Journal of Organic Chemistry 58, no. 10 (1993): 2910–12. http://dx.doi.org/10.1021/jo00062a044.

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41

Wang, Wuyi, Stan V. D'Andrea, Jeremiah P. Freeman, and Jacob Szmuszkovicz. "Metal-halogen exchange reactions of 1,5-diiodonaphthalene. Synthesis of 1,5-disubstituted naphthalene derivatives." Journal of Organic Chemistry 56, no. 8 (1991): 2914–15. http://dx.doi.org/10.1021/jo00008a059.

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42

Yamashita, Hiroshi, Toshi-aki Kobayashi, Teruyuki Hayashi, and Masato Tanaka. "Novel Halogen Exchange Reactions between Halosilanes and Rh(I) or Ir(I) Complexes." Chemistry Letters 18, no. 3 (1989): 471–74. http://dx.doi.org/10.1246/cl.1989.471.

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43

Artamkina, Galina A., Petr K. Sazonov, Vasily A. Ivushkin, and Irina P. Beletskaya. "Formation of cis-[Rf(CO)Re(CO)4Hal]Na complexes as an evidence of halogen-metal exchange between [Re(CO)5]Na and polyfluorinated aryl and vinyl halides." Canadian Journal of Chemistry 76, no. 6 (1998): 970–72. http://dx.doi.org/10.1139/v98-051.

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Halo(acyl)rhenate complexes cis-[Rf(CO)Re(CO)4Hal]Na (Hal = Cl, Br; Rf = C6F5, trans-(CF3)3CCF== CF) are the primary products of the reactions of [Re(CO)5]Na with the corresponding aryl or vinyl halides RfHal.Key words: pentacarbonylrhenate anion, carbonylmetallates, halogen-metal exchange, nucleophilic aromatic substitution, nucleophilic vinylic substitution.

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44

Mikołajczyk, Marian, Barbara Ziemnicka, Jan Krzywański, Marek Cypryk, and Bartłomiej Gostyński. "Nucleophilic Substitution at Tetracoordinate Phosphorus. Stereochemical Course and Mechanisms of Nucleophilic Displacement Reactions at Phosphorus in Diastereomeric cis- and trans-2-Halogeno-4-methyl-1,3,2-dioxaphosphorinan-2-thiones: Experimental and DFT Studies." Molecules 26, no. 12 (2021): 3655. http://dx.doi.org/10.3390/molecules26123655.

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Geometrical cis- and trans- isomers of 2-chloro-, 2-bromo- and 2-fluoro-4-methyl-1,3,2-dioxaphosphorinan-2-thiones were obtained in a diastereoselective way by (a) sulfurization of corresponding cyclic PIII-halogenides, (b) reaction of cyclic phosphorothioic acids with phosphorus pentachloride and (c) halogen–halogen exchange at PIV-halogenide. Their conformation and configuration at the C4-ring carbon and phosphorus stereocentres were studied by NMR (1H, 31P) methods, X-ray analysis and density functional (DFT) calculations. The stereochemistry of displacement reactions (alkaline hydrolysis,

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45

Piller, Fabian M., Tomke Bresser, Markus K. R. Fischer, and Paul Knochel. "Preparation of Functionalized Cyclic Enol Phosphates by Halogen−Magnesium Exchange and Directed Deprotonation Reactions." Journal of Organic Chemistry 75, no. 13 (2010): 4365–75. http://dx.doi.org/10.1021/jo100763f.

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46

COOKE, M. P. JUN, and D. GOPAL. "ChemInform Abstract: Tandem Metal-Halogen Exchange-Initiated Conjugate Addition Reactions of Conjugated Acetylenic Esters." ChemInform 25, no. 23 (2010): no. http://dx.doi.org/10.1002/chin.199423062.

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47

COOKE, M. P. JUN. "ChemInform Abstract: Metal-Halogen Exchange-Initiated Intramolecular Conjugate Addition Reactions of Conjugated Acetylenic Esters." ChemInform 25, no. 12 (2010): no. http://dx.doi.org/10.1002/chin.199412084.

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48

ROZOV, L. A., R. A. LESSOR, L. V. KUDZMA, and K. RAMIG. "ChemInform Abstract: The Fluoromethyl Ether Sevoflurane as a Fluoride Source in Halogen-Exchange Reactions." ChemInform 29, no. 28 (2010): no. http://dx.doi.org/10.1002/chin.199828046.

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49

Boche, Gernot, Michael Schimeczek, Jerzy Cioslowski, and Pawel Piskorz. "The Role of Ate Complexes in Halogen(Metalloid)–Metal Exchange Reactions: A Theoretical Study." European Journal of Organic Chemistry 1998, no. 9 (1998): 1851–60. http://dx.doi.org/10.1002/(sici)1099-0690(199809)1998:9<1851::aid-ejoc1851>3.0.co;2-n.

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50

van den Berghe, E. V., G. P. van der Kelen, and Z. Eeckhaut. "A Study of Halogen Exchange Reactions Between Methyltin Halides by N. M. R. Spectroscopy." Bulletin des Sociétés Chimiques Belges 76, no. 1-2 (2010): 79–91. http://dx.doi.org/10.1002/bscb.19670760109.

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