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Journal articles on the topic 'Dehydrohalogenation'

Author: Grafiati

Published: 4 June 2021

Last updated: 18 February 2022

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1

Halton, B., CJ Randall, GJ Gainsford, and WT Robinson. "Studies in the Cycloproparene Series: Competitive Pathways in the Dehydrohalogenation Route to 2-Halobicyclo[4.1.0]Hepta-1,3,5-Trienes." Australian Journal of Chemistry 40, no. 3 (1987): 475. http://dx.doi.org/10.1071/ch9870475.

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The (1α,2β,3α,6α)-2,3,7,7-tetrahalobicyclo[4.1.0]heptanes (8a-c), whose structures have been determined by X-ray methods, give 2-halobicyclo[4.1.0]hepta-1,3,5-trienes (5) upon dehydrohalogenation. The 'mixed' halide (8c) and partly labelled [7-13c]-(8b,c) have revealed the presence of competing pathways in these conversions. By comparison, dehydrohalogenations of the (1α,3α,4β,6α)-3,4,7,7-tetrahalobicyclo[4.1.0]heptanes (3) give unrearranged 3-halobicyclo[4.1.0]-hepta-1,3,5-trienes (4).

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2

Suárez, Angela R., Alejandra G. Suárez, Sandra E. Martín, and María R. Mazzieri. "Dehydrobromination of 1,1-diaryl-1,2-dibromoalkanes catalyzed by iron and iron bromides. An ion-pair-mediated reaction?" Canadian Journal of Chemistry 73, no. 1 (January 1, 1995): 56–60. http://dx.doi.org/10.1139/v95-008.

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The participation of ion-paired Lewis acid/Lewis base in the dehydrohalogenations of 1,2-dibromo-1,1 -diarylalkanes catalyzed by Fe0 and by Fe(II) and Fe(III) bromides was investigated. The reactivities of the catalyst employed were correlated with their chemical hardness. The influence of para substituents on the phenyl rings of the substrates and the results obtained in Lewis-acid-catalyzed and thermal dehydrobromination of the same compounds were compared. The experimental results could not be explained in terms of a Lewis-acid-catalyzed dehydrobromination. Keywords: dehydrohalogenation, bromoalkanes, Lewis acid catalysts, ion-pair mechanism.

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3

Ahubelem, Nwakamma, Mohammednoor Altarawneh, and Bogdan Z. Dlugogorski. "Dehydrohalogenation of ethyl halides." Tetrahedron Letters 55, no. 35 (August 2014): 4860–68. http://dx.doi.org/10.1016/j.tetlet.2014.07.009.

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4

Bock, Hans, and Hans Peter Wolf. "Oberflächen-Reaktionen, 9 Dehydrohalogenierungen von Halogenkohlenwasserstoffen an Raney-Nickel / Surface Reactions, 9 Dehydrohalogenation of Halohydrocarbons at Raney Nickel." Zeitschrift für Naturforschung B 44, no. 6 (June 1, 1989): 699–714. http://dx.doi.org/10.1515/znb-1989-0614.

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Raney nickel, a highly reactive and air-sensitive solid, if prepared and investigated under oxygen-free conditions, exhibits interesting catalytic properties. Using photoelectron spectroscopy for real-time gas analysis in a flow reactor, the following results are obtained with alkyl and acylhalides: Dehydrohalogenation temperatures are lowered relative to thermal HHal elimination up to 350 K. Monochloro and bromo propanes and butenes yield propene and butadiene, respectively. 1,1-Dichloro ethane or 1,1-dibromo propane only split off one HHal and form chloroethene or 1-bromopropene-2. HCl elimination from 2-methyl propionic acid chloride, expectedly, produces dimethyl ketene. Most interesting, however, is the ring opening of monobromo cyclobutane to 1-bromo-butene-3, observed already at room temperature, which strongly suggests the intermediate formation of a chemisorbed surface carbene at Raney nickel. The formation of hexadiene-1,5 as a by-product in the HCl elimination of 1-chloropropane, i. e. a surface carbene dimer, indicates their presence also in other dehydrohalogenations heterogeneously catalyzed by Raney nickel.

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5

Ho, Po-Yuen, Hartmut Komber, Kilian Horatz, Takuya Tsuda, Stefan C. B. Mannsfeld, Evgenia Dmitrieva, Olivier Blacque, Ulrike Kraft, Henning Sirringhaus, and Franziska Lissel. "Synthesis and characterization of a semiconducting and solution-processable ruthenium-based polymetallayne." Polymer Chemistry 11, no. 2 (2020): 472–79. http://dx.doi.org/10.1039/c9py01090d.

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6

Ji, Wenzhi, Chen-Long Li, Hui Chen, Zhi-Xiang Yu, and Xuebin Liao. "A newly designed heterodiene and its application to construct six-membered heterocycles containing an N–O bond." Chemical Communications 55, no. 80 (2019): 12012–15. http://dx.doi.org/10.1039/c9cc05694g.

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7

Martí-Rujas, Javier, and Fang Guo. "Dehydrohalogenation reactions in second-sphere coordination complexes." Dalton Transactions 50, no. 34 (2021): 11665–80. http://dx.doi.org/10.1039/d1dt02099d.

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8

Evsyukov, S. E., Yu P. Kudryavtsev, and Yu V. Korshak. "Chemical dehydrohalogenation of halogen-containing polymers." Russian Chemical Reviews 60, no. 4 (April 30, 1991): 373–90. http://dx.doi.org/10.1070/rc1991v060n04abeh001083.

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9

Mishakov, Ilya V., Alexander F. Bedilo, Ryan M. Richards, Vladimir V. Chesnokov, Alexander M. Volodin, Vladimir I. Zaikovskii, Roman A. Buyanov, and Kenneth J. Klabunde. "Nanocrystalline MgO as a Dehydrohalogenation Catalyst." Journal of Catalysis 206, no. 1 (February 2002): 40–48. http://dx.doi.org/10.1006/jcat.2001.3474.

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10

Santandrea, Jeffrey, Eric Godin, and Shawn K. Collins. "A synthetic guide to alkynyl sulfides." Organic & Biomolecular Chemistry 18, no. 26 (2020): 4885–93. http://dx.doi.org/10.1039/d0ob00908c.

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Alkynyl sulfides can be prepared via dehydrohalogenation, nucleophilic and electrophilic thiol alkynylation and catalytic C_sp–S bond formation. Each method presents certain advantages and limitations.

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11

Navrátil, Michal, Erica N. Faria, Geve Panahy, Ivana Císařová, Jose M. Goicoechea, and Petr Štěpnička. "Novel ferrocenyl functionalised phosphinecarboxamides: synthesis, characterisation and coordination." Dalton Transactions 49, no. 25 (2020): 8645–51. http://dx.doi.org/10.1039/d0dt01908a.

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12

Koch, Heinz F., Gerrit Lodder, and Judith G. Koch. "Effect of beta-fluoride on dehydrohalogenation reactions." Journal of Fluorine Chemistry 54, no. 1-3 (September 1991): 99. http://dx.doi.org/10.1016/s0022-1139(00)83609-x.

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13

Dureja, P., S. Walia, and S. K. Mukerjee. "Superoxide mediated dehydrohalogenation of photodieldrin and photoaldrin." Tetrahedron Letters 28, no. 8 (January 1987): 895–96. http://dx.doi.org/10.1016/s0040-4039(01)81017-0.

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14

Suarez, Angela R., Maria R. Mazzieri, and Alejandra G. Suarez. "Dehydrohalogenation of vic-dibromoethanes catalyzed by iron." Journal of the American Chemical Society 111, no. 2 (January 1989): 763–64. http://dx.doi.org/10.1021/ja00184a072.

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15

Kopka, Ihor E., Michael A. Nowak, and Michael W. Rathke. "Dehydrohalogenation Reactions Using Hindered Lithium Dialkylamide Bases." Synthetic Communications 16, no. 1 (January 1986): 27–34. http://dx.doi.org/10.1080/00397918608057684.

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16

Evsyukov, S. E., B. Thomas, and R. B. Heimann. "Chemical dehydrohalogenation of poly(ethylene-alt-chlorotrifluoroethylene)." Materials Chemistry and Physics 66, no. 1 (September 2000): 34–40. http://dx.doi.org/10.1016/s0254-0584(00)00263-7.

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17

Kontsur, Y., G. Shapoval, and A. Pud. "Electrochemical dehydrohalogenation of poly(vinylchloride) in pyridine." Polymer Degradation and Stability 60, no. 2-3 (January 1998): 515–16. http://dx.doi.org/10.1016/s0141-3910(97)00074-8.

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18

Carrow, B. P., H. Bakhru, P. I. Wang, Y. Chen, and J. J. Senkevich. "Dehydrohalogenation in Alpha-Functionalized Poly-p-xylylenes." Chemical Vapor Deposition 12, no. 4 (April 2006): 239–44. http://dx.doi.org/10.1002/cvde.200506426.

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19

Yorimitsu, H., K. Oshima, T. Kobayashi, and H. Ohmiya. "Dehydrohalogenation of Alkyl Halides with Complementary Regioselectivity." Synfacts 2008, no. 11 (October 23, 2008): 1199. http://dx.doi.org/10.1055/s-0028-1083465.

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20

Suarez, Angela R., and Maria R. Mazzieri. "Dehydrohalogenation of vic-dihaloalkanes over silica gel." Journal of Organic Chemistry 52, no. 6 (March 1987): 1145–47. http://dx.doi.org/10.1021/jo00382a033.

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21

Carmello, D., and L. Memo. "Production of vinyl chloride by catalytic dehydrohalogenation." Zeolites 15, no. 3 (March 1995): 284. http://dx.doi.org/10.1016/0144-2449(95)90058-6.

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22

Boitsov, V. M., R. R. Kostikov, A. P. Molchanov, A. V. Stepakov, and M. S. Baird. "Dehydrohalogenation of substituted diethyl halocyclopropane-1,1-dicarboxylates." Russian Journal of Organic Chemistry 40, no. 12 (December 2004): 1760–63. http://dx.doi.org/10.1007/s11178-005-0095-0.

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23

Kuznetsov, N. Yu, R. M. Tikhov, I. A. Godovikov, V. N. Khrustalev, and Yu N. Bubnov. "New enolate-carbodiimide rearrangement in the concise synthesis of 6-amino-2,3-dihydro-4-pyridinones from homoallylamines." Organic & Biomolecular Chemistry 14, no. 18 (2016): 4283–98. http://dx.doi.org/10.1039/c6ob00293e.

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Three-step synthesis of 6-amino-2,3-dihydro-4-pyridinones from homoallylamines involving NBS-mediated cyclization of N-(3-butenyl)ureas to 6-(bromomethyl)-2-iminourethanes, dehydrohalogenation and a novel rearrangement as a key step has been developed.

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24

Kyri, A. W., G. Schnakenburg, and R. Streubel. "A novel route to C-unsubstituted 1,2-oxaphosphetane and 1,2-oxaphospholane complexes." Chemical Communications 52, no. 55 (2016): 8593–95. http://dx.doi.org/10.1039/c6cc04667c.

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The synthesis of 1,2-oxaphosphetane complexes 7 and 1,2-oxaphospholane complex 12 bearing only substituents at phosphorus is reported using the reaction of Li/Cl phosphinidenoid complex 2 with 2-iodoethanol or 3-bromo-propane-1-ol and the subsequent dehydrohalogenation using KHMDS.

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25

Heyn, Richard H., and Kenneth G. Caulton. "Dehydrohalogenation for facile generation of unsaturated ruthenium(0)." Journal of the American Chemical Society 115, no. 8 (April 1993): 3354–55. http://dx.doi.org/10.1021/ja00061a054.

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26

Shapoval, G. S., and Y. V. Kontsur. "Electrochemical Initiation of Surface Dehydrohalogenation of Polyvinylchloride Films." Journal of Macromolecular Science, Part A 32, no. 1 (January 1, 1995): 49–54. http://dx.doi.org/10.1080/10601329508020313.

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27

Cataldo, F. "Synthesis of polyynes by dehydrohalogenation of chlorinated paraffins." Die Angewandte Makromolekulare Chemie 264, no. 1 (February 1, 1999): 65–72. http://dx.doi.org/10.1002/(sici)1522-9505(19990201)264:1<65::aid-apmc65>3.0.co;2-9.

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28

Lee, Yeong-Beom, Hong-Ku Shim, and Seung-Won Ko. "Silyl-Substituted Poly(thienylenevinylene) via Heteroaromatic Dehydrohalogenation Polymerization." Macromolecular Rapid Communications 24, no. 8 (May 2003): 522–26. http://dx.doi.org/10.1002/marc.200390080.

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29

Bohle, D. S., and J. B. Helms. "Synthesis of β-Hematin by Dehydrohalogenation of Hemin." Biochemical and Biophysical Research Communications 193, no. 2 (June 1993): 504–8. http://dx.doi.org/10.1006/bbrc.1993.1652.

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30

Sirovsky, F. S. "Phase-transfer and micellar catalysis in dehydrohalogenation reaction." Russian Chemical Bulletin 44, no. 11 (November 1995): 2026–38. http://dx.doi.org/10.1007/bf00696701.

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31

Dargelos, M., ME Borredon, and A. Gaset. "Synthesis of Epihalohydrins by Dehydrohalogenation of Glycerol Dihalohydrins - Utilization of a Basic Ion-Exchange Resin." Australian Journal of Chemistry 45, no. 8 (1992): 1327. http://dx.doi.org/10.1071/ch9921327.

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Dehydrohalogenation of a mixture of glycerol 1,3- and 2,3-dihalohydrins by a strong basic ion-exchange resin (IRA 440 and A 26) at room temperature in an organic medium quantitatively leads to the corresponding epihalohydrin (1a; X = Cl), and (1b; X = Br) in a very short reaction time. Hydrolysis of the epihalohydrin does not occur under these conditions.

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32

Magerramov, A. M., M. N. Magerramov, I. A. Aliev, A. M. Mustafaev, and U. F. Askerova. "Dehydrohalogenation of haloalkylarenes in the synthesis of alkenylaromatic hydrocarbons." Russian Journal of Organic Chemistry 48, no. 2 (February 2012): 293–95. http://dx.doi.org/10.1134/s1070428012020212.

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33

VASIN, V. A., S. G. KOSTRYUKOV, and V. V. RAZIN. "ChemInform Abstract: Halogenosulfonation-Dehydrohalogenation of 1-Phenyltricyclo(4.1.0.02,7) heptane." ChemInform 27, no. 44 (August 4, 2010): no. http://dx.doi.org/10.1002/chin.199644095.

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34

Biswas, Sunanda, Matthias Müller, Christina Tönshoff, Klaus Eichele, Cäcilia Maichle-Mössmer, Adrian Ruff, Bernd Speiser, and Holger F. Bettinger. "The Overcrowded Borazine Derivative of Hexabenzotriphenylene Obtained through Dehydrohalogenation." European Journal of Organic Chemistry 2012, no. 24 (June 29, 2012): 4634–39. http://dx.doi.org/10.1002/ejoc.201200322.

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35

Arumugam, Subramaniam, and John G. Verkade. "P(CH3NCH2CH2)3N: A Nonionic Superbase for Efficient Dehydrohalogenation." Journal of Organic Chemistry 62, no. 14 (July 1997): 4827–28. http://dx.doi.org/10.1021/jo962310z.

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36

Yoshizawa, Kazunari, Kazuyoshi Tanaka, and Tokio Yamabe. "Synthesis of Poly(m-aniline) by Dehydrohalogenation ofm-Chloroaniline." Chemistry Letters 19, no. 8 (August 1990): 1311–14. http://dx.doi.org/10.1246/cl.1990.1311.

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37

Rodenas, E., and C. Otero. "Base-Catalysed Dehydrohalogenation — NS of Dicofol in CTAB Micelles." Tenside Surfactants Detergents 27, no. 6 (December 1, 1990): 396–98. http://dx.doi.org/10.1515/tsd-1990-270612.

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38

Rulev, Alexander Yu, Alexey R. Romanov, Alexander V. Popov, Evgeniy V. Kondrashov, and Sergey V. Zinchenko. "Reaction of Bromoenones with Amidines: A Simple Catalyst-Free Approach to Trifluoromethylated Pyrimidines." Synthesis 52, no. 10 (March 9, 2020): 1512–22. http://dx.doi.org/10.1055/s-0040-1707969.

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A facile one-pot synthesis of trifluoromethylated pyrimidines has been achieved by the treatment of fluorinated 2-bromoenones with aryl- and alkylamidines. The assembly of pyrimidine core proceeds by the cascade reactions via aza-Michael addition–intramolecular cyclization–dehydrohalogenation/dehydration sequence. This strategy is featured by high selectivity and mild reaction conditions giving the target heterocycles in high yields (up to 99%). The unique influence of trifluoromethyl group on the reaction path is demonstrated.

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39

Perrone, Luca, Laura Prati, and Michele Rossi. "Removal of chlorinated organic compounds from water by catalytic dehydrohalogenation." Applied Catalysis B: Environmental 15, no. 3-4 (February 1998): 241–46. http://dx.doi.org/10.1016/s0926-3373(97)00051-9.

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40

Soderquist, John A., Jaime Vaquer, Michael J. Diaz, Anil M. Rane, Frederick G. Bordwell, and Shizhong Zhang. "Triisopropylsilanol: A new type of phase transfer catalyst for dehydrohalogenation." Tetrahedron Letters 37, no. 15 (April 1996): 2561–64. http://dx.doi.org/10.1016/0040-4039(96)00330-9.

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41

Kobayashi, Tsuneyuki, Hirohisa Ohmiya, Hideki Yorimitsu, and Koichiro Oshima. "Cobalt-Catalyzed Regioselective Dehydrohalogenation of Alkyl Halides with Dimethylphenylsilylmethylmagnesium Chloride." Journal of the American Chemical Society 130, no. 34 (August 2008): 11276–77. http://dx.doi.org/10.1021/ja804277x.

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42

Poirier, Donald, Marie Bérubé, Fatima Kamal, and Jenny Roy. "A Dehydrohalogenation Methodology for Synthesizing Terminal Olefins under Mild Conditions." Synthesis 2006, no. 18 (August 21, 2006): 3085–91. http://dx.doi.org/10.1055/s-2006-950204.

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43

Jha, S. C., and N. N. Joshi. "Intramolecular Dehydrohalogenation during Base-Mediated Reaction of Diols with Dihaloalkanes." Journal of Organic Chemistry 67, no. 11 (May 2002): 3897–99. http://dx.doi.org/10.1021/jo011046t.

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44

SIROVSKII, F. S. "ChemInform Abstract: Phase-Transfer and Micellar Catalysis in Dehydrohalogenation Reaction." ChemInform 27, no. 17 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199617296.

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45

Minsker, K. S., R. B. Pancheshnikova, and G. E. Zaikov. "Peculiarities of the thermal dehydrohalogenation of some halogen-containing polymers." Polymer Degradation and Stability 19, no. 1 (January 1987): 1–27. http://dx.doi.org/10.1016/0141-3910(87)90009-7.

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46

Plack, Volker, Jens R. Goerlich, Holger Th�nnessen, Peter G. Jones, and Reinhard Schmutzler. "The reaction of triphenylmethylhalophosphines with tetrachloro-orthobenzoquinone: Oxidation?isomerization?dehydrohalogenation." Heteroatom Chemistry 10, no. 4 (1999): 277–80. http://dx.doi.org/10.1002/(sici)1098-1071(1999)10:4<277::aid-hc3>3.0.co;2-5.

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47

Liu, Li, Ming-Xuan Li, and Wai-Yeung Wong. "Synthesis and Luminescent Properties of Mercury(II) Polyynes Containing Derivatized Benzene in the Backbone." Australian Journal of Chemistry 58, no. 11 (2005): 799. http://dx.doi.org/10.1071/ch05215.

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Group 12 mercury(ii) polyyne polymers containing derivatized benzene spacers were prepared in good yields using Hagihara’s dehydrohalogenation reaction of HgCl2 with HC≡C(C6H2R)2C≡CH (R = 4,5-dioctyloxy, 2,5-dihexadecyloxy) at room temperature in a basic medium. The structures of these polymers were confirmed by standard spectroscopic methods and their luminescent properties were examined. Our investigations indicate that two polymers exhibit different luminescence properties due to different position of the substituents on the benzene spacer.

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48

Beattie, Nicola J., Craig L. Francis, Andris J. Liepa, and G. Paul Savage. "Spiroheterocycles via Regioselective Cycloaddition Reactions of Nitrile Oxides with 5-Methylene-1H-pyrrol-2(5H)-ones." Australian Journal of Chemistry 63, no. 3 (2010): 445. http://dx.doi.org/10.1071/ch09479.

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Substituted 5-methylene-1H-pyrrol-2(5H)-ones underwent a 1,3-dipolar cycloaddition reaction with nitrile oxides to give the corresponding spiro heterocycles. Critical to this reaction was the development of a biphasic system for base-induced dehydrohalogenation of hydroximoyl chlorides, to give nitrile oxides, in the presence of a base-sensitive dipolarophile. A substituted N-tolyl 5-methylene-1H-pyrrol-2(5H)-one exhibited atropisomerism, which in turn led to a 4:1 facial selectivity during cycloaddition.

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49

Ferrando, German, and Kenneth G. Caulton. "Dehydrohalogenation as a Source of OsHnCl(PPh3)3(n= 1, 3)." Inorganic Chemistry 38, no. 18 (September 1999): 4168–70. http://dx.doi.org/10.1021/ic981402z.

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50

Roberts, A. L., P. M. Jeffers, N. L. Wolfe, and P. M. Gschwent. "Structure‐reactivity relationships in dehydrohalogenation reactions of polychlorinated and polybrominated alkanes." Critical Reviews in Environmental Science and Technology 23, no. 1 (January 1993): 1–39. http://dx.doi.org/10.1080/10643389309388440.

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