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Journal articles on the topic 'Superacid Chemistry'

Author: Grafiati

Published: 10 March 2023

Last updated: 11 March 2023

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1

Kotun, Stefan P., and Darryl D. DesMarteau. "Superacid-induced ring-opening reactions of fluorinated heterocycles." Canadian Journal of Chemistry 67, no. 11 (November 1, 1989): 1724–28. http://dx.doi.org/10.1139/v89-265.

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HF/AsF5 and HF/SbF5 superacid mixtures react with fluorinated small-ring heterocycles such as 1,2-oxazetidines and oxetanes with consequent addition of HF to give alcohol and amine ring-opened products in high yield. Excess HF serves as solvent and reactant. Ring compounds containing both nitrogen and oxygen as heteroatoms protonate predominantly on nitrogen; a case with competing O-protonation arises in the case of a chloro-substituted oxazetidine. In general, rings containing two heteroatoms retain the heteroatom–heteroatom bond and it is a carbon–heteroatom bond that opens. The resulting OH and NH functional groups are not protonated and lost in the superacid medium due to the instability of the highly fluorinated cations that would be left behind. Most of the heterocycles react at or below room temperature, although the very weakly basic 2,2-bis(trifluoromethyl)-3,3,4,4-tetrafluorooxetane requires the stronger HF/SbF5 superacid system and more severe conditions. Keywords: superacids, hydrogen fluoride, ring opening, fluorinated oxazetidines, fluorinated oxetanes.

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2

Rasul, Golam, G. K. Surya Prakash, and George A. Olah. "Chemistry in Superacids. 15. Gitonic Protodiazonium and Bisdiazonium Dications and Their Potential Role in Superacid Chemistry." Journal of the American Chemical Society 116, no. 20 (October 1994): 8985–90. http://dx.doi.org/10.1021/ja00099a016.

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3

Enami, Shinichi, Logan A. Stewart, Michael R. Hoffmann, and Agustín J. Colussi. "Superacid Chemistry on Mildly Acidic Water." Journal of Physical Chemistry Letters 1, no. 24 (December 3, 2010): 3488–93. http://dx.doi.org/10.1021/jz101402y.

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4

Knoecer, Larecia, Daniel DeSchepper, and Douglas A. Klumpp. "Superacid-Induced Reactions of Nefopam." Organic Chemistry International 2010 (June 13, 2010): 1–5. http://dx.doi.org/10.1155/2010/496818.

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The analgesic drug nefopam reacts in superacidic media to form a dicationic superelectrophiles by ring opening. The dication species is capable of reacting with arenes in Friedel-Crafts-type conversions. This chemistry is used to prepare novel derivatives of nefopam.

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5

Olah, George A., Nikolai Hartz, Golam Rasul, Arwed Burrichter, and G. K. Surya Prakash. "Chemistry in Superacids. Part 18. Ester Cleavage in Superacid Media Involving Diprotonated Gitonic Carboxonium Dications." Journal of the American Chemical Society 117, no. 24 (June 1995): 6421–27. http://dx.doi.org/10.1021/ja00129a001.

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6

Hartz, Nikolai, Golam Rasul, and George A. Olah. "Chemistry in superacids. 10. Role of oxonium, sulfonium, and carboxonium dications in superacid-catalyzed reactions." Journal of the American Chemical Society 115, no. 4 (February 1993): 1277–85. http://dx.doi.org/10.1021/ja00057a009.

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7

Kulsha, Andrey V., and Dmitry I. Sharapa. "Superhalogen and Superacid." Journal of Computational Chemistry 40, no. 26 (June 29, 2019): 2293–300. http://dx.doi.org/10.1002/jcc.26007.

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8

Wang, Siqi, Yaroslav V. Zonov, Victor M. Karpov, Olga A. Luzina, and Tatyana V. Mezhenkova. "Carbonylation of Polyfluorinated 1-Arylalkan-1-ols and Diols in Superacids." Molecules 27, no. 24 (December 10, 2022): 8757. http://dx.doi.org/10.3390/molecules27248757.

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We describe the carbonylation of a series of mono and dihydroxy derivatives of polyfluorinated alkylbenzenes and benzocycloalkenes with OH groups at benzylic positions using carbon monoxide in the presence of a superacid (TfOH, a TfOH–SbF5 mixture, or a FSO3H–SbF5 mixture). It was shown that the superacid-catalyzed addition of CO to various primary and secondary polyfluorinated alcohols and diols gives the corresponding mono- and dicarboxylic acids or lactones. The efficiency of various superacids depending on alcohol structure was evaluated, and FSO3H–SbF5 yielded the best results in most transformations. The addition of CO to secondary 1-arylalkan-1-ols containing vicinal fluorine atoms was found to be accompanied by elimination of HF with the formation of α,β-unsaturated aryl-carboxylic acids. In contrast to primary and secondary alcohols, conversion of tertiary perfluoro-1,1-diarylalkan-1-ols into carbonylation products is not complete, and the resulting carboxylic acids are easily decarboxylated after water treatment of the reaction mixture.

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9

Olah, George A., and Omar Farooq. "Chemistry in superacids. 7. Superacid-catalyzed isomerization of endo- to exo-trimethylenenorbornane (tetrahydrodicyclopentadiene) and to adamantane." Journal of Organic Chemistry 51, no. 26 (December 1986): 5410–13. http://dx.doi.org/10.1021/jo00376a067.

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10

Mazej, Zoran, Primož Benkič, Alain Tressaud, and Boris Žemva. "Palladium Chemistry in Anhydrous HF/AsF5 Superacid Medium." European Journal of Inorganic Chemistry 2004, no. 9 (May 2004): 1827–34. http://dx.doi.org/10.1002/ejic.200300681.

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11

OLAH, G. A., N. HARTZ, G. RASUL, A. BURRICHTER, and G. K. S. PRAKASH. "ChemInform Abstract: Chemistry in Superacids. Part 18. Ester Cleavage in Superacid Media Involving Diprotonated Gitonic Carboxonium Dications." ChemInform 26, no. 42 (August 17, 2010): no. http://dx.doi.org/10.1002/chin.199542052.

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12

Ahlberg, Per, Annika Karlsson, Alain Goeppert, Sten O. Nilsson Lill, Peter Dinér, and Jean Sommer. "Solvated CH5+ in Liquid Superacid." Chemistry 7, no. 9 (May 4, 2001): 1936–43. http://dx.doi.org/10.1002/1521-3765(20010504)7:9<1936::aid-chem1936>3.0.co;2-t.

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13

Ahlberg, Per, Annika Karlsson, Alain Goeppert, Sten O. Nilsson Lill, Peter Dinér, and Jean Sommer. "Solvated CH5+ in Liquid Superacid." Chemistry - A European Journal 7, no. 12 (June 18, 2001): 2501. http://dx.doi.org/10.1002/1521-3765(20010618)7:12<2501::aid-chem25011>3.0.co;2-w.

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14

Benítez, V. M., Carlos R. Vera, C. L. Pieck, F. G. Lacamoire, J. C. Yori, J. M. Grau, and J. M. Parera. "Silica supported superacid isomerization catalysts." Catalysis Today 107-108 (October 2005): 651–56. http://dx.doi.org/10.1016/j.cattod.2005.07.046.

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15

Gillespie, Ronald J., and Jack Liang. "Superacid solutions in hydrogen fluoride." Journal of the American Chemical Society 110, no. 18 (August 1988): 6053–57. http://dx.doi.org/10.1021/ja00226a020.

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16

HARTZ, N., G. RASUL, and G. A. OLAH. "ChemInform Abstract: Chemistry in Superacids. Part 10. Role of Oxonium, Sulfonium, and Carboxonium Dications in Superacid-Catalyzed Reactions." ChemInform 24, no. 25 (August 20, 2010): no. http://dx.doi.org/10.1002/chin.199325043.

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17

Prudius, Svitlana, Natalia Hes, Volodymyr Trachevskiy, Oleg Khyzhun, and Volodymyr Brei. "Superacid ZrO2–SiO2–SnO2 Mixed Oxide: Synthesis and Study." Chemistry & Chemical Technology 15, no. 3 (August 15, 2021): 336–42. http://dx.doi.org/10.23939/chcht15.03.336.

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Superacid ternary ZrO2 SiO2 SnO2 oxide has been synthesized by the sol-gel method with a different atomic ratio Zr:Si:Sn. The highest strength of acid sites has been observed in the ranges of 20 ≤ Zr4+ ≤ 29, 60 ≤ Si4+ ≤ 67, 11 ≤ Sn4+ ≤ 20 at.%. According to the XPS spectra and 119Sn, 29Si MAS NMR spectra of ZrO2 SiO2 SnO2 a partial shift of electron density from zirconium to silicon ions was observed resulting in the formation of superacid Lewis sites. It was shown that superacid Zr29Si60Sn11 mixed oxide efficiently catalyzes acylation of toluene with acetic anhydride at 423 K in a flow reactor with 45% conversion of anhydride at 100% selectivity towards p-methylacetophenone.

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18

Jacquesy, Jean-Claude. "Reactivity of Vinca alkaloids in superacid." Journal of Fluorine Chemistry 127, no. 11 (November 2006): 1484–87. http://dx.doi.org/10.1016/j.jfluchem.2006.09.008.

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19

Eller, P. Gary, LarnedB Asprey, ScottA Kinkead, ElizabethM Larson, CharlesF Pace, WilliamH Woodruff, and LarryR Avens. "Superacid chemistry of actinide and lanthanide metals, oxides and fluorides." Journal of Fluorine Chemistry 35, no. 1 (February 1987): 97. http://dx.doi.org/10.1016/0022-1139(87)95074-3.

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20

Klumpp, Douglas A., Gregorio V. Sanchez, Sharon L. Aguirre, Yun Zhang, and Sarah de Leon. "Chemistry of Dicationic Electrophiles: Superacid-Catalyzed Reactions of Amino Acetals." Journal of Organic Chemistry 67, no. 14 (July 2002): 5028–31. http://dx.doi.org/10.1021/jo0111558.

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21

Klumpp, Douglas A., Yiliang Zhang, Patrick J. Kindelin, and Siufu Lau. "Superacid-catalyzed reactions of pyridinecarboxaldehydes." Tetrahedron 62, no. 25 (June 2006): 5915–21. http://dx.doi.org/10.1016/j.tet.2006.04.022.

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22

Henkelmann, Marcel, Andreas Omlor, Michael Bolte, Volker Schünemann, Hans-Wolfram Lerner, Jozef Noga, Peter Hrobárik, and Matthias Wagner. "A free boratriptycene-type Lewis superacid." Chemical Science 13, no. 6 (2022): 1608–17. http://dx.doi.org/10.1039/d1sc06404e.

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23

Tracy, Adam F., Matthew P. Abbott, and Douglas A. Klumpp. "Superacid-Promoted Hydroxyalkylation of 1,2-Indandiones." Synthetic Communications 43, no. 16 (June 3, 2013): 2171–77. http://dx.doi.org/10.1080/00397911.2012.693239.

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24

Becker, Kurt A., and Stanisław Kowalak. "Superacid sites in zeolite H-mordenite." Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases 82, no. 7 (1986): 2151. http://dx.doi.org/10.1039/f19868202151.

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25

Bogoczek, Romuald, and Joanna Surowiec. "Superacid Systems on Solid Carriers." Chemie Ingenieur Technik 59, no. 2 (February 1987): 178–79. http://dx.doi.org/10.1002/cite.330590236.

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26

Miyatake, Kenji, Takuya Shimura, Takefumi Mikami, and Masahiro Watanabe. "Aromatic ionomers with superacid groups." Chemical Communications, no. 42 (2009): 6403. http://dx.doi.org/10.1039/b913260k.

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27

Kennedy, Sean H., Makafui Gasonoo, and Douglas A. Klumpp. "Superelectrophilic carbocations: preparation and reactions of a substrate with six ionizable groups." Beilstein Journal of Organic Chemistry 15 (July 9, 2019): 1515–20. http://dx.doi.org/10.3762/bjoc.15.153.

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A substrate has been prepared having two triarylmethanol centers and four pyridine-type substituent groups. Upon ionization in the Brønsted superacid CF3SO3H, the substrate undergoes two types of reactions. In the presence of only the superacid, the highly ionized intermediate(s) provide a double cyclization product having two pyrido[1,2-a]indole rings. With added benzene, an arylation product is obtained. A mechanism is proposed involving tetra-, penta-, or hexacationic species.

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28

Chagnault, Vincent, Sébastien Thibaudeau, Marie-Paule Jouannetaud, Jean-Claude Jacquesy, Alain Cousson, and Christian Bachmann. "Rearrangement and fluorination of quinidinone in superacid." Journal of Fluorine Chemistry 128, no. 1 (January 2007): 55–59. http://dx.doi.org/10.1016/j.jfluchem.2006.09.018.

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29

Abboud, J. L. M., O. Castaño, J. Elguero, M. Herreros, N. Jagerovic, R. Notario, and K. Sak. "Superacid chemistry in the gas phase: Dissociative proton attachment to halomethanes." International Journal of Mass Spectrometry and Ion Processes 175, no. 1-2 (May 1998): 35–40. http://dx.doi.org/10.1016/s0168-1176(98)00110-4.

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30

Laali, Kenneth Khosrow, Edward Gelerinter, and Robert Filler. "Janusene and tetrafluorojanusene in superacid media; radical cation formation and chemistry." Journal of Fluorine Chemistry 53, no. 1 (June 1991): 107–26. http://dx.doi.org/10.1016/s0022-1139(00)82243-5.

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31

Vuong, Hien, Michael R. Stentzel, and Douglas A. Klumpp. "Superacid-promoted synthesis of quinoline derivatives." Tetrahedron Letters 61, no. 12 (March 2020): 151630. http://dx.doi.org/10.1016/j.tetlet.2020.151630.

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32

Zhang, Yun, Aaron McElrea, Gregorio V. Sanchez, Dat Do, Alma Gomez, Sharon L. Aguirre, Rendy, and Douglas A. Klumpp. "Dicationic Electrophiles from Olefinic Amines in Superacid⊥." Journal of Organic Chemistry 68, no. 13 (June 2003): 5119–22. http://dx.doi.org/10.1021/jo030024z.

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33

Vlad, P. F., N. D. Ungur, and V. B. Perutskii. "Superacid cyclization of homo- and bishomoisoprenoid acids." Chemistry of Heterocyclic Compounds 27, no. 3 (March 1991): 246–49. http://dx.doi.org/10.1007/bf00474221.

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34

Tun, Zin-Min, Amy J. Heston, Matthew J. Panzner, Vincenzo Scionti, Doug A. Medvetz, Brian D. Wright, Nicholas A. Johnson, et al. "Group 13 Superacid Adducts of [PCl2N]3." Inorganic Chemistry 55, no. 7 (March 14, 2016): 3283–93. http://dx.doi.org/10.1021/acs.inorgchem.5b02341.

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35

Tsuchimura, Tomotaka, and Takeshi Kawabata. "Novel Acid Amplifier Generating Disulfonimide as Superacid." Journal of Photopolymer Science and Technology 30, no. 6 (2017): 645–49. http://dx.doi.org/10.2494/photopolymer.30.645.

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36

Grinco, Marina, Veaceslav Kulciţki, Nicon Ungur, Wieslaw Jankowski, Tadeusz Chojnacki, and Pavel F Vlad. "Superacid-Catalyzed Cyclization of Methyl (6Z)-Geranylfarnesoates." Helvetica Chimica Acta 90, no. 6 (June 2007): 1223–29. http://dx.doi.org/10.1002/hlca.200790122.

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37

Zolotukhin1, Mikhail G., Serguie Fomine, Luz Maria Lazo, Ma Del Carmen G. Hernández, M. T. Guzmán-Gutiérrez, Alberto Ruiz-Trevino, Detlev Fritsch, David Cuellas Cuellas, and Juan M. Fernandez-G. "A Novel Approach to the Synthesis of High Performance and Functional Polymers." High Performance Polymers 19, no. 5-6 (October 2007): 638–48. http://dx.doi.org/10.1177/0954008307081204.

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A novel series of linear, high molecular weight high performance and functional polymers were synthesized by a one-pot, superacid-catalyzed polyhydroxylakylation reaction of carbonyl compounds containing electron-withdrawing substituents, adjacent or relatively close to a carbocation center with non-activated aromatic hydrocarbons. The reactions were performed at room temperature in the Brønsted superacid CF3SO3H (trifluoromethanesulfonic acid, TFSA) and in a mixture of TFSA with methylene chloride, which was used as both solvent and a medium for generation of electrophilic species from the carbonyl component. Polycondensations of 1,1,1-trifluoroacetone, 2,2,2-trifluoroacetohenone, 2,7-dinitrofluorenone, acenaphthenequinone and isatin with aromatic hydrocarbons proceed readily in the presence of superacid at room temperature. The polymers obtained were found to be soluble in the common organic solvents, and flexible transparent films could be cast from the solutions. 1H and 13C NMR analyses of the polymers synthesized revealed their linear, highly regular structure. The polymers also possess high thermostability.

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38

Umansky, Benjamin S., Manoj Bhinde, Chao-Yang Hsu, and Chen-Sh Huang. "5629257 Solid superacid catalysts comprising platinum metal." Journal of Molecular Catalysis A: Chemical 125, no. 2-3 (November 1997): 155. http://dx.doi.org/10.1016/s1381-1169(98)80023-x.

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39

Liu, Fei, Agnès Martin-Mingot, F. Lecornué, Marie-Paule Jouannetaud, Alfonso Maresca, Sebastien Thibaudeau, and Claudiu T. Supuran. "Carbonic Anhydrases inhibitory effects of new benzenesulfonamides synthesized by using superacid chemistry." Journal of Enzyme Inhibition and Medicinal Chemistry 27, no. 6 (December 14, 2011): 886–91. http://dx.doi.org/10.3109/14756366.2011.638921.

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40

Klumpp, Douglas A., Gregorio V. Sanchez Jr., Sharon L. Aguirre, Yun Zhang, and Sarah de Leon. "ChemInform Abstract: Chemistry of Dicationic Electrophiles: Superacid-Catalyzed Reactions of Amino Acetals." ChemInform 33, no. 47 (May 18, 2010): no. http://dx.doi.org/10.1002/chin.200247062.

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41

Zolotukhin, Mikhail G., Serguei Fomine, Luz María Lazo, Roberto Salcedo, Luis E. Sansores, Gerardo G. Cedillo, Howard M. Colquhoun, Juan M. Fernandez-G, and Alexei F. Khalizov. "Superacid-Catalyzed Polycondensation of Acenaphthenequinone with Aromatic Hydrocarbons." Macromolecules 38, no. 14 (July 2005): 6005–14. http://dx.doi.org/10.1021/ma0503460.

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42

Bagno, Alessandro, Jozef Bukala, and George A. Olah. "Chemistry in superacids. 8. Superacid-catalyzed carbonylation of methane, methyl halides, methyl alcohol, and dimethyl ether to methyl acetate and acetic acid." Journal of Organic Chemistry 55, no. 14 (July 1990): 4284–89. http://dx.doi.org/10.1021/jo00301a015.

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43

Kögel, Julius F., Alexey Y. Timoshkin, Artem Schröder, Enno Lork, and Jens Beckmann. "Al(OCArF3)3 – a thermally stable Lewis superacid." Chemical Science 9, no. 43 (2018): 8178–83. http://dx.doi.org/10.1039/c8sc02981d.

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Al(OCArF3)₃ (Ar^F = C₆F₅) – a readily accessible, adduct free and highly stable Lewis superacid with an extreme fluoride ion affinity to store in your glove box!

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44

Chen, F. R., G. Coudurier, J. F. Joly, and J. C. Vedrine. "Superacid and Catalytic Properties of Sulfated Zirconia." Journal of Catalysis 143, no. 2 (October 1993): 616–26. http://dx.doi.org/10.1006/jcat.1993.1304.

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45

Hartmann, Deborah, Marcel Schädler, and Lutz Greb. "Bis(catecholato)silanes: assessing, rationalizing and increasing silicon's Lewis superacidity." Chemical Science 10, no. 31 (2019): 7379–88. http://dx.doi.org/10.1039/c9sc02167a.

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46

Nakamura, Satoshi, Masaru Tanaka, Tooru Taniguchi, Masanobu Uchiyama, and Tomohiko Ohwada. "Stereoselectivity of Superacid-Catalyzed Pictet−Spengler Cyclization Reactions." Organic Letters 5, no. 12 (June 2003): 2087–90. http://dx.doi.org/10.1021/ol034526a.

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47

Jin, Tong-Shou, Yan-Ran Ma, Xu Sun, Dan Liang, and Tong-Shuang Li. "Facile Preparation of 1,1-Diacetates from Aldehydes with Acetic Anhydride Catalysed by TiO2/SO42- solid superacid." Journal of Chemical Research 2000, no. 2 (February 2000): 96–97. http://dx.doi.org/10.3184/030823400103166526.

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48

Jin, Tong-Shou, Guo-Liang Feng, Mi-Na Yang, and Tong-Shuang Li. "An Efficient and Convenient Procedure for Preparation of N-Sulfonylimines Catalysed by TiO2/SO42- Solid Superacid." Journal of Chemical Research 2003, no. 9 (September 2003): 591–93. http://dx.doi.org/10.3184/030823403322597432.

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49

Ghosh, Suman Kr, Avinash Dhamija, Young Ho Ko, Jaeyeon An, Moon Young Hur, Deepak Ramdas Boraste, Jongcheol Seo, Eunsung Lee, Kyeng Min Park, and Kimoon Kim. "Superacid-Mediated Functionalization of Hydroxylated Cucurbit[n]urils." Journal of the American Chemical Society 141, no. 44 (October 21, 2019): 17503–6. http://dx.doi.org/10.1021/jacs.9b09639.

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50

Jin, Tong-Shou, Jun-Jie Guo, Ya-Hui Yin, Su-Ling Zhang, and Tong-Shuang Li. "TiO2/SO42-, An Efficient Catalyst for the Methoxymethylation of Alcohols." Journal of Chemical Research 2002, no. 4 (April 2002): 188–89. http://dx.doi.org/10.3184/030823402103171627.

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