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Isolation of Protonated Arenes (Wheland Intermediates) with BArF and Carborane Anions. A Novel Crystalline Superacid

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Department of Chemistry, University of California, Riverside, California 92521-0403
Department of Chemistry, The University of Auckland, Private Bag, Auckland, New Zealand
Cite this: J. Am. Chem. Soc. 1999, 121, 26, 6314–6315
Publication Date (Web):June 16, 1999
https://doi.org/10.1021/ja981861z
Copyright © 1999 American Chemical Society
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Details of the synthetic procedures and characterization of products 15 and the X-ray crystal structure determination of 2. This material is available free of charge via the Internet at http://pubs.acs.org.

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  3. Erich Kleinpeter, Andreas Koch. Benzenium Ion: Aromatic as the π-Complex or Antiaromatic as the σ-Complex Being Somewhat Similar to the Cyclopentadienyl Cation. The Journal of Physical Chemistry A 2019, 123 (20) , 4443-4451. https://doi.org/10.1021/acs.jpca.9b03121
  4. Hanxue Xia, Yong Zhang, Athula B. Attygalle. Experimental and Theoretical Studies on Gas-Phase Fragmentation Reactions of Protonated Methyl Benzoate: Concomitant Neutral Eliminations of Benzene, Carbon Dioxide, and Methanol. Journal of the American Society for Mass Spectrometry 2018, 29 (8) , 1601-1610. https://doi.org/10.1007/s13361-018-1997-8
  5. Maxime Romain, Cassandre Quinton, Thierry Roisnel, Emmanuel Jacques, Joëlle Rault-Berthelot, and Cyril Poriel . A Dihydrodinaphthoheptacene. The Journal of Organic Chemistry 2018, 83 (4) , 1891-1897. https://doi.org/10.1021/acs.joc.7b02834
  6. Konstantin Chernichenko, Markus Lindqvist, Bianka Kótai, Martin Nieger, Kristina Sorochkina, Imre Pápai, and Timo Repo . Metal-Free sp2-C–H Borylation as a Common Reactivity Pattern of Frustrated 2-Aminophenylboranes. Journal of the American Chemical Society 2016, 138 (14) , 4860-4868. https://doi.org/10.1021/jacs.6b00819
  7. Bhusan Thapaliya, Suman Debnath, Navamoney Arulsamy, and Dean M. Roddick . Synthesis and Structural Characterization of an Unusual Platinum π-Arene Complex: (η6-C6H3Me3)Pt[(C2F5)2PMe]Me+. Organometallics 2015, 34 (16) , 4018-4022. https://doi.org/10.1021/acs.organomet.5b00410
  8. Christopher A. Reed . Myths about the Proton. The Nature of H+ in Condensed Media. Accounts of Chemical Research 2013, 46 (11) , 2567-2575. https://doi.org/10.1021/ar400064q
  9. Christos Douvris and Josef Michl . Update 1 of: Chemistry of the Carba-closo-dodecaborate(−) Anion, CB11H12–. Chemical Reviews 2013, 113 (10) , PR179-PR233. https://doi.org/10.1021/cr400059k
  10. Simon Duttwyler, Anna M. Butterfield, and Jay S. Siegel . Arenium Acid Catalyzed Deuteration of Aromatic Hydrocarbons. The Journal of Organic Chemistry 2013, 78 (5) , 2134-2138. https://doi.org/10.1021/jo302201a
  11. Michael A. Duncan . Infrared Laser Spectroscopy of Mass-Selected Carbocations. The Journal of Physical Chemistry A 2012, 116 (47) , 11477-11491. https://doi.org/10.1021/jp309037d
  12. Anne Kraft, Jennifer Beck, Gunther Steinfeld, Harald Scherer, Daniel Himmel, and Ingo Krossing . Synthesis and Application of Strong Brønsted Acids Generated from the Lewis Acid Al(ORF)3 and an Alcohol. Organometallics 2012, 31 (21) , 7485-7491. https://doi.org/10.1021/om300776a
  13. Zvonimir B. Maksić, Borislav Kovačević, and Robert Vianello . Advances in Determining the Absolute Proton Affinities of Neutral Organic Molecules in the Gas Phase and Their Interpretation: A Theoretical Account. Chemical Reviews 2012, 112 (10) , 5240-5270. https://doi.org/10.1021/cr100458v
  14. Matthew Nava and Christopher A. Reed . Triethylsilyl Perfluoro-Tetraphenylborate, [Et3Si+][F20-BPh4–], a Widely Used Nonexistent Compound. Organometallics 2011, 30 (17) , 4798-4800. https://doi.org/10.1021/om200636u
  15. Steven L. Matthews and D. Michael Heinekey . An Oxidized Active Site Model for the FeFe Hydrogenase: Reduction with Hydrogen Gas. Inorganic Chemistry 2011, 50 (17) , 7925-7927. https://doi.org/10.1021/ic2009573
  16. Steven L. Matthews and D. Michael Heinekey. A Carbonyl-Rich Bridging Hydride Complex Relevant to the Fe−Fe Hydrogenase Active Site. Inorganic Chemistry 2010, 49 (21) , 9746-9748. https://doi.org/10.1021/ic1017328
  17. Alessandro Del Grosso, Robin G. Pritchard, Chris A. Muryn and Michael J. Ingleson. Chelate Restrained Boron Cations for Intermolecular Electrophilic Arene Borylation. Organometallics 2010, 29 (1) , 241-249. https://doi.org/10.1021/om900893g
  18. Jeramie J. Adams, Navamoney Arulsamy and Dean M. Roddick. Acceptor Pincer Coordination Chemistry of Platinum: Reactivity Properties of (CF3PCP)Pt(L)+ (L = NC5F5, C2H4). Organometallics 2009, 28 (4) , 1148-1157. https://doi.org/10.1021/om8008876
  19. Sayanti Basu, Navamoney Arulsamy and Dean M. Roddick. Synthesis of [(dfepe)Pt(Me)(NC5F5)]+B(C6F5)4−, a Highly Active Ethylene Dimerization Catalyst. Organometallics 2008, 27 (15) , 3659-3665. https://doi.org/10.1021/om8003509
  20. Orson L. Sydora,, Stefan M. Kilyanek, and, Richard F. Jordan. Cationic Zirconocene and Hafnocene Aryl Complexes. Organometallics 2007, 26 (19) , 4746-4755. https://doi.org/10.1021/om700436z
  21. Robin Panisch,, Michael Bolte, and, Thomas Müller. Structure and Bonding in Bissilylated Arenium Ions. Organometallics 2007, 26 (14) , 3524-3529. https://doi.org/10.1021/om0702375
  22. Stefanie Körbe,, Peter J. Schreiber, and, Josef Michl. Chemistry of the Carba-closo-dodecaborate(−) Anion, CB11H12-. Chemical Reviews 2006, 106 (12) , 5208-5249. https://doi.org/10.1021/cr050548u
  23. Takeshi Kawase and, Hiroyuki Kurata. Ball-, Bowl-, and Belt-Shaped Conjugated Systems and Their Complexing Abilities:  Exploration of the Concave−Convex π−π Interaction. Chemical Reviews 2006, 106 (12) , 5250-5273. https://doi.org/10.1021/cr0509657
  24. Blanka Kašná,, Roman Jambor,, Libor Dostál,, Ivana Císařová,, Jaroslav Holeček, and, Bohumil Štíbr. Stabilization of Triaryltin(IV) Cations Containing an O,C,O-Coordinating Pincer-Type Ligand. Isolation of a New [Ag(1-CB11H12)3]2- Anion. Organometallics 2006, 25 (21) , 5139-5144. https://doi.org/10.1021/om060516c
  25. Barbara Chiavarino,, Maria Elisa Crestoni, and, Simonetta Fornarini, , Otto Dopfer, , Joel Lemaire and, Philippe Maître. IR Spectroscopic Features of Gaseous C7H7O+ Ions:  Benzylium versus Tropylium Ion Structures. The Journal of Physical Chemistry A 2006, 110 (30) , 9352-9360. https://doi.org/10.1021/jp0628380
  26. Zong-Quan Wu,, Xue-Bin Shao,, Chuang Li,, Jun-Li Hou,, Kui Wang,, Xi-Kui Jiang, and, Zhan-Ting Li. Hydrogen-Bonding-Driven Preorganized Zinc Porphyrin Receptors for Efficient Complexation of C60, C70, and C60 Derivatives. Journal of the American Chemical Society 2005, 127 (49) , 17460-17468. https://doi.org/10.1021/ja056509h
  27. Shaun Garratt,, Andrew G. Carr,, Gerhard Langstein, and, Manfred Bochmann. Isobutene Polymerization and Isobutene-Isoprene Copolymerization Catalyzed by Cationic Zirconocene Hydride Complexes. Macromolecules 2003, 36 (12) , 4276-4287. https://doi.org/10.1021/ma034320p
  28. Michael P. Jensen,, Steven J. Lange,, Mark P. Mehn,, Emily L. Que, and, Lawrence Que, Jr.. Biomimetic Aryl Hydroxylation Derived from Alkyl Hydroperoxide at a Nonheme Iron Center. Evidence for an FeIVO Oxidant. Journal of the American Chemical Society 2003, 125 (8) , 2113-2128. https://doi.org/10.1021/ja028478l
  29. Adem Rifat,, Nathan J. Patmore,, Mary F. Mahon, and, Andrew S. Weller. Rhodium Phosphines Partnered with the Carborane Monoanions [CB11H6Y6]- (Y = H, Br). Synthesis and Evaluation as Alkene Hydrogenation Catalysts. Organometallics 2002, 21 (14) , 2856-2865. https://doi.org/10.1021/om020077r
  30. Lee D. Henderson,, Warren E. Piers,, Geoffry J. Irvine, and, Robert McDonald. Anion Stability in Stannylium, Oxonium, and Silylium Salts of the Weakly Coordinating Anion [C6F4-1,2-{B(C6F5)2}2(μ-OCH3)]-. Organometallics 2002, 21 (2) , 340-345. https://doi.org/10.1021/om010750x
  31. Michael L. McKee. Proposed Fluorination Mechanism of CB5H6- and CB9H10- with HF. Evidence of Kinetic Control in the Formation of 2-CB5H5F- and 6-CB9H9F-. Inorganic Chemistry 2001, 40 (22) , 5612-5619. https://doi.org/10.1021/ic010176h
  32. Yi Han,, C. Jeff Harlan,, Philipp Stoessel,, Brian J. Frost,, Jack R. Norton,, Susie Miller,, Brian Bridgewater, and, Qiang Xu. Rhenium Oxo Complexes of a Chelating Diyne Ligand. Synthesis and Study of the Kinetics of Protonation. Inorganic Chemistry 2001, 40 (13) , 2942-2952. https://doi.org/10.1021/ic0100931
  33. Chi-Wing Tsang,, Qingchuan Yang,, Eric Tung-Po Sze,, Thomas C. W. Mak,, Dominic T. W. Chan, and, Zuowei Xie. Weakly Coordinating Nature of a Carborane Cage Bearing Different Halogen Atoms. Synthesis and Structural Characterization of Icosahedral Mixed Halocarborane Anions, 1-H-CB11Y5X6- (X, Y = Cl, Br, I). Inorganic Chemistry 2000, 39 (25) , 5851-5858. https://doi.org/10.1021/ic000354r
  34. S. M. Hubig and, J. K. Kochi. Structure and Dynamics of Reactive Intermediates in Reaction Mechanisms. σ- and π-Complexes in Electrophilic Aromatic Substitutions. The Journal of Organic Chemistry 2000, 65 (21) , 6807-6818. https://doi.org/10.1021/jo000706b
  35. Chi-Wing Tsang,, Qingchuan Yang,, Eric Tung-Po Sze,, Thomas C. W. Mak,, Dominic T. W. Chan, and, Zuowei Xie. Synthesis and Structural Characterization of Highly Chlorinated, Brominated, Iodinated, and Methylated Carborane Anions, 1-H-CB9X9-, 1-NH2-CB9X9- (X = Cl, Br, I), and 1-H-CB9(CH3)9- . Inorganic Chemistry 2000, 39 (16) , 3582-3589. https://doi.org/10.1021/ic000137q
  36. Ilmar A. Koppel,, Peeter Burk,, Ivar Koppel,, Ivo Leito,, Takaaki Sonoda, and, Masaaki Mishima. Gas-Phase Acidities of Some Neutral Brønsted Superacids:  A DFT and ab Initio Study. Journal of the American Chemical Society 2000, 122 (21) , 5114-5124. https://doi.org/10.1021/ja0000753
  37. Daniel R. Evans,, Nathanael L. P. Fackler,, Zuowei Xie,, Clifton E. F. Rickard,, Peter D. W. Boyd, and, Christopher A. Reed. π-Arene/Cation Structure and Bonding. Solvation versus Ligand Binding in Iron(III) Tetraphenylporphyrin Complexes of Benzene, Toluene, p-Xylene, and [60]Fullerene. Journal of the American Chemical Society 1999, 121 (37) , 8466-8474. https://doi.org/10.1021/ja9910816
  38. Tao He, Guoqiang Wang, Peng-Wei Long, Sebastian Kemper, Elisabeth Irran, Hendrik F. T. Klare, Martin Oestreich. Intramolecular Friedel–Crafts alkylation with a silylium-ion-activated cyclopropyl group: formation of tricyclic ring systems from benzyl-substituted vinylcyclopropanes and hydrosilanes. Chemical Science 2021, 12 (2) , 569-575. https://doi.org/10.1039/D0SC05553K
  39. Suman Debnath, Sayanti Basu, Bradley M. Schmidt, Jeramie J. Adams, Navamoney Arulsamy, Dean M. Roddick. Platinum ethylene dimerization catalysts: Diphosphine vs. diimine ancillary ligand effects. Polyhedron 2020, 181 , 114461. https://doi.org/10.1016/j.poly.2020.114461
  40. Sławomir J. Grabowski, David Casanova, Elena Formoso, Jesus M. Ugalde. Tetravalent Oxygen and Sulphur Centres Mediated by Carborane Superacid: Theoretical Analysis. ChemPhysChem 2019, 20 (19) , 2443-2450. https://doi.org/10.1002/cphc.201900687
  41. Junichiro Kanazawa, Yu Kitazawa, Masanobu Uchiyama. Recent Progress in the Synthesis of the Monocarba‐ closo ‐dodecaborate(−) Anions. Chemistry – A European Journal 2019, 25 (39) , 9123-9132. https://doi.org/10.1002/chem.201900174
  42. Ian M. Riddlestone, Anne Kraft, Julia Schaefer, Ingo Krossing. Die Schöne (WCA) und das (kationische) Biest: Neues aus der Chemie von und mit schwach koordinierenden Anionen. Angewandte Chemie 2018, 130 (43) , 14178-14221. https://doi.org/10.1002/ange.201710782
  43. Ian M. Riddlestone, Anne Kraft, Julia Schaefer, Ingo Krossing. Taming the Cationic Beast: Novel Developments in the Synthesis and Application of Weakly Coordinating Anions. Angewandte Chemie International Edition 2018, 57 (43) , 13982-14024. https://doi.org/10.1002/anie.201710782
  44. Bastien Michelet, Hélène Carreyre, Frédéric Lecornué, Agnès Mingot, Sébastien Thibaudeau. Superelectrophilic activation in superacid HF/SbF5: Expanding molecular diversity in nitrogen-containing compounds series by fluorination. Journal of Fluorine Chemistry 2018, 214 , 68-79. https://doi.org/10.1016/j.jfluchem.2018.04.017
  45. Qian Wu, Zheng-Wang Qu, Lukas Omann, Elisabeth Irran, Hendrik F. T. Klare, Martin Oestreich. Spaltung nicht aktivierter Si-C(sp 3 )-Bindungen mit Reedschen Carboransäuren: Bildung bekannter und unbekannter Silyliumionen. Angewandte Chemie 2018, 130 (29) , 9317-9320. https://doi.org/10.1002/ange.201805637
  46. Qian Wu, Zheng-Wang Qu, Lukas Omann, Elisabeth Irran, Hendrik F. T. Klare, Martin Oestreich. Cleavage of Unactivated Si−C(sp 3 ) Bonds with Reed's Carborane Acids: Formation of Known and Unknown Silylium Ions. Angewandte Chemie International Edition 2018, 57 (29) , 9176-9179. https://doi.org/10.1002/anie.201805637
  47. Zhe-Chen Wang, Ditte L. Thomsen, Edwin L. Motell, Marin S. Robinson, Rustam Garrey, Veronica M. Bierbaum, Charles H. DePuy. The gas-phase methylation of benzene and toluene. International Journal of Mass Spectrometry 2018, 429 , 6-13. https://doi.org/10.1016/j.ijms.2017.03.009
  48. Daniel Himmel, Valentin Radtke, Burkhard Butschke, Ingo Krossing. Grundlegende Bemerkungen zur Azidität. Angewandte Chemie 2018, 130 (16) , 4471-4498. https://doi.org/10.1002/ange.201709057
  49. Daniel Himmel, Valentin Radtke, Burkhard Butschke, Ingo Krossing. Basic Remarks on Acidity. Angewandte Chemie International Edition 2018, 57 (16) , 4386-4411. https://doi.org/10.1002/anie.201709057
  50. . Heterosubstitution. 2017,,, 795-862. https://doi.org/10.1002/9781119390541.ch10
  51. S. Thibaudeau, H. Carreyre, A. Mingot. Synthesis of Fluorinated Nitrogen-Containing Compounds Through Superelectrophilic Activation in Superacid HF/SbF5∗∗This work is dedicated to Pr Jean-Claude Jacquesy with great consideration.. 2017,,, 349-388. https://doi.org/10.1016/B978-0-12-803740-9.00013-5
  52. Eiji Tsurumaki. Carborane Acid: Protonation of the Weakest Bases by the Strongest Acid. Journal of Synthetic Organic Chemistry, Japan 2017, 75 (4) , 360-361. https://doi.org/10.5059/yukigoseikyokaishi.75.360
  53. Jennifer Phelps, Jeffrey L. Butikofer, Bhusan Thapaliya, Eric Gale, Courtney L. Vowell, Suman Debnath, Navamoney Arulsamy, Dean M. Roddick. Structural and reactivity properties of perfluoroalkylphosphine complexes of platinum(0). Polyhedron 2016, 116 , 197-203. https://doi.org/10.1016/j.poly.2016.04.045
  54. Russell N. Grimes. Icosahedral Carboranes. 2016,,, 249-281. https://doi.org/10.1016/B978-0-12-801894-1.00008-1
  55. Tobias A. Engesser, Martin R. Lichtenthaler, Mario Schleep, Ingo Krossing. Reactive p-block cations stabilized by weakly coordinating anions. Chemical Society Reviews 2016, 45 (4) , 789-899. https://doi.org/10.1039/C5CS00672D
  56. Douglas A. Klumpp. Electrophilic Aromatic Substitution. 2015,,, 1-31. https://doi.org/10.1002/9781118754887.ch1
  57. N. M. Bravaya, E. E. Faingol’d, A. N. Galiullin, O. N. Babkina, S. L. Saratovskikh, A. V. Chernyak, V. D. Makhaev. Alkylation of toluene with dichloromethane in the presence of triisobutylaluminum and perfluorophenylborates. Russian Chemical Bulletin 2015, 64 (9) , 2076-2082. https://doi.org/10.1007/s11172-015-1120-2
  58. Franziska Scholz, Daniel Himmel, Lea Eisele, Wiebke Unkrig, Arthur Martens, Peter Schlüter, Ingo Krossing. The Acidity of the HBr/AlBr 3 System: Stabilization of Crystalline Protonated Arenes and Their Acidity in Bromoaluminate Ionic Liquids. Chemistry - A European Journal 2015, 21 (20) , 7489-7502. https://doi.org/10.1002/chem.201405952
  59. Kalon J. Iversen, David J. D. Wilson, Jason L. Dutton. A Computational Study on a Strategy for Isolating a Stable Cyclopentadienyl Cation. Chemistry – A European Journal 2014, 20 (43) , 14132-14138. https://doi.org/10.1002/chem.201403748
  60. Andreas Franken, John D. Kennedy, Jude Clapper, Larry G. Sneddon. Monocarbaborane Anions with 10 or 12 Vertices. 2014,,, 174-185. https://doi.org/10.1002/9781118744994.ch34
  61. Franziska Scholz, Daniel Himmel, Lea Eisele, Wiebke Unkrig, Ingo Krossing. Die Supersäure HBr/AlBr 3 : Protonierung von Benzol und ausgeordnete Kristallstruktur von [C 6 H 7 ] + [Al 2 Br 7 ] −. Angewandte Chemie 2014, 126 (6) , 1715-1718. https://doi.org/10.1002/ange.201308120
  62. Franziska Scholz, Daniel Himmel, Lea Eisele, Wiebke Unkrig, Ingo Krossing. The Superacid HBr/AlBr 3 : Protonation of Benzene and Ordered Crystal Structure of [C 6 H 7 ] + [Al 2 Br 7 ] −. Angewandte Chemie International Edition 2014, 53 (6) , 1689-1692. https://doi.org/10.1002/anie.201308120
  63. Hui-Fen Chen, Yu-Jong Wu. Structure, stability, and vibrational fundamentals of low-lying isomers of. Computational and Theoretical Chemistry 2013, 1006 , 100-104. https://doi.org/10.1016/j.comptc.2012.11.014
  64. C. Knapp. Weakly Coordinating Anions: Halogenated Borates and Dodecaborates. 2013,,, 651-679. https://doi.org/10.1016/B978-0-08-097774-4.00125-X
  65. E.Y.-X. Chen, S.J. Lancaster. Weakly Coordinating Anions: Highly Fluorinated Borates. 2013,,, 707-754. https://doi.org/10.1016/B978-0-08-097774-4.00127-3
  66. Elvis A. Twum, Timothy J. Woodman, Wenyi Wang, Michael D. Threadgill. Observation by NMR of cationic Wheland-like intermediates in the deiodination of protected 1-iodonaphthalene-2,4-diamines in acidic media. Organic & Biomolecular Chemistry 2013, 11 (36) , 6208. https://doi.org/10.1039/c3ob41386a
  67. Mohammed Bahou, Yu-Jong Wu, Yuan-Pern Lee. A new method for investigating infrared spectra of protonated benzene (C 6 H 7 + ) and cyclohexadienyl radical ( c -C 6 H 7 ) using para -hydrogen. The Journal of Chemical Physics 2012, 136 (15) , 154304. https://doi.org/10.1063/1.3703502
  68. Andy M. Chapman, Mairi F. Haddow, Duncan F. Wass. Cationic Group 4 Metallocene-(o-Phosphanylaryl)oxido Complexes: Synthetic Routes to Transition-Metal Frustrated Lewis Pairs. European Journal of Inorganic Chemistry 2012, 2012 (9) , 1546-1554. https://doi.org/10.1002/ejic.201100968
  69. Andrea Vöge, Detlef Gabel. Boron in Weakly Coordinating Anions and Ionic Liquids. 2011,,, 807-826. https://doi.org/10.1201/b11199-37
  70. Sibayan Mukherjee, Ajay K. Bauri, Sumanta Bhattacharya. Determination of binding strength for the supramolecular complexation of a designed bisporphyrin with C60, C70 and their derivatives employing absorption spectrophotometric, fluorescence and quantum chemical calculations. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2011, 79 (5) , 1952-1958. https://doi.org/10.1016/j.saa.2011.05.099
  71. Debabrata Pal, Sumanta Bhattacharya. Absorption spectrophotometric, fluorescence and theoretical investigations on supramolecular interaction of a designed bisporphyrin with C60 and C70. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2011, 79 (3) , 638-645. https://doi.org/10.1016/j.saa.2011.03.050
  72. Russell N. Grimes. Icosahedral carboranes. 2011,,, 267-299. https://doi.org/10.1016/B978-0-12-374170-7.00010-0
  73. . Heavy Analogs of Carbenium Ions: Si-, Ge-, Sn- and Pb-Centered Cations. 2010,,, 1-43. https://doi.org/10.1002/9780470669266.ch1
  74. Pau Farràs, Clara Viñas, Reijo Sillanpää, Francesc Teixidor, Milagros Rey. The nature of the chlorination reaction in [1-C6H5-1-CB9H9]− boron clusters. Dalton Transactions 2010, 39 (33) , 7684. https://doi.org/10.1039/c0dt00433b
  75. Cyril Poriel, Frédéric Barrière, Damien Thirion, Joëlle Rault-Berthelot. Encumbered DiSpiro[Fluorene-IndenoFluorene]: Mechanistic Insights. Chemistry - A European Journal 2009, 15 (48) , 13304-13307. https://doi.org/10.1002/chem.200902006
  76. Simon Duttwyler, Yun Zhang, Anthony Linden, Christopher A. Reed, Kim K. Baldridge, Jay S. Siegel. Synthesis and Crystal Structure of a Silyl-Stabilized Allyl Cation Formed by Disruption of an Arene by a Protonation-Hydrosilylation Sequence. Angewandte Chemie 2009, 121 (21) , 3845-3848. https://doi.org/10.1002/ange.200900098
  77. Simon Duttwyler, Yun Zhang, Anthony Linden, Christopher A. Reed, Kim K. Baldridge, Jay S. Siegel. Synthesis and Crystal Structure of a Silyl-Stabilized Allyl Cation Formed by Disruption of an Arene by a Protonation-Hydrosilylation Sequence. Angewandte Chemie International Edition 2009, 48 (21) , 3787-3790. https://doi.org/10.1002/anie.200900098
  78. Andrea Vöge, Enno Lork, Behice Şebnem Sesalan, Detlef Gabel. N-arylammonio- and N-pyridinium-substituted derivatives of dodecahydro-closo-dodecaborate(2-). Journal of Organometallic Chemistry 2009, 694 (11) , 1698-1703. https://doi.org/10.1016/j.jorganchem.2008.12.053
  79. Sheshanath V. Bhosale, Sidhanath V. Bhosale, Steven J. Langford, Dragan Krsta. Construction of trimeric porphyrin-fullerene-porphyrin stacks within surface-derived pores of nano-scale dimensions. Chemical Communications 2009, 271 (22) , 3166. https://doi.org/10.1039/b903699g
  80. Eugen Justus, Klaus Rischka, James F. Wishart, Kristina Werner, Detlef Gabel. Trialkylammoniododecaborates: Anions for Ionic Liquids with Potassium, Lithium and Protons as Cations. Chemistry - A European Journal 2008, 14 (6) , 1918-1923. https://doi.org/10.1002/chem.200701427
  81. Simon Duttwyler, Quyen-Quyen Do, Anthony Linden, Kim K. Baldridge, Jay S. Siegel. Synthesis of 2,6-Diarylphenyldimethylsilyl Cations: Polar-π Distribution of Cation Character. Angewandte Chemie 2008, 120 (9) , 1743-1746. https://doi.org/10.1002/ange.200705291
  82. Simon Duttwyler, Quyen-Quyen Do, Anthony Linden, Kim K. Baldridge, Jay S. Siegel. Synthesis of 2,6-Diarylphenyldimethylsilyl Cations: Polar-π Distribution of Cation Character. Angewandte Chemie International Edition 2008, 47 (9) , 1719-1722. https://doi.org/10.1002/anie.200705291
  83. John Dymon, Ryan Wibby, Jesse Kleingardner, Joseph M. Tanski, Ilia A. Guzei, John D. Holbrey, Anna S. Larsen. Designing ionic liquids with boron cluster anions: alkylpyridinium and imidazolium [nido-C2B9H11] and [closo-CB11H12] carborane salts. Dalton Transactions 2008, 99 (22) , 2999. https://doi.org/10.1039/b802374c
  84. Paul G. Hayes, Warren E. Piers, Masood Parvez. Arene Complexes of β-Diketiminato Supported Organoscandium Cations: Mechanism of Arene Exchange and Alkyne Insertion in Solvent Separated Ion Pairs. Chemistry - A European Journal 2007, 13 (9) , 2632-2640. https://doi.org/10.1002/chem.200601087
  85. Clara Viñas, Anna Laromaine, Francesc Teixidor, Hana Horáková, Aleš Langauf, Radim Vespalec, Ignasi Mata, Elies Molins. Synthesis and investigation of the boron cluster anion [7-(2′-pyridyl)-7,8-nido-dicarbaundecaborate] and its protonated form. Dalton Transactions 2007, 92 (31) , 3369. https://doi.org/10.1039/b705160c
  86. P. Vilmercati, C. Castellarin Cudia, R. Larciprete, C. Cepek, G. Zampieri, L. Sangaletti, S. Pagliara, A. Verdini, A. Cossaro, L. Floreano, A. Morgante, L. Petaccia, S. Lizzit, C. Battocchio, G. Polzonetti, A. Goldoni. Molecular orientations, electronic properties and charge transfer timescale in a Zn-porphyrin/C70 donor–acceptor complex for solar cells. Surface Science 2006, 600 (18) , 4018-4023. https://doi.org/10.1016/j.susc.2006.01.116
  87. Otto Dopfer. IR spectroscopic strategies for the structural characterization of isolated and microsolvated arenium ions. Journal of Physical Organic Chemistry 2006, 19 (8-9) , 540-551. https://doi.org/10.1002/poc.1053
  88. Morten Bjørgen, Francesca Bonino, Bjørnar Arstad, Stein Kolboe, Karl-Petter Lillerud, Adriano Zecchina, Silvia Bordiga. Persistent Methylbenzenium Ions in Protonated Zeolites: The Required Proton Affinity of the Guest Hydrocarbon. ChemPhysChem 2005, 6 (2) , 232-235. https://doi.org/10.1002/cphc.200400422
  89. Henk Buck. Quantum chemical study of alternating N/B and N/C ? bonds in (un)charged even-membered 4n and 4n+2 cyclic systems and their related open systems. International Journal of Quantum Chemistry 2005, 101 (1) , 73-83. https://doi.org/10.1002/qua.20193
  90. Thomas Müller. Cations of Group 14 Organometallics. 2005,,, 155-215. https://doi.org/10.1016/S0065-3055(05)53005-3
  91. Christopher A. Reed. Carborane acids. New “strong yet gentle” acids for organic and inorganic chemistry. Chem. Commun. 2005, 17 (13) , 1669-1677. https://doi.org/10.1039/B415425H
  92. Amy L. Kieran, Sofia I. Pascu, Thibaut Jarrosson, Jeremy K. M. Sanders. Inclusion of C60 into an adjustable porphyrin dimer generated by dynamic disulfide chemistry. Chemical Communications 2005, 318 (10) , 1276. https://doi.org/10.1039/b417951j
  93. Agnieszka Grzelka, Julian Chojnowski, Marek Cypryk, Witold Fortuniak, Peter C. Hupfield, Richard G. Taylor. Polysiloxanol condensation and disproportionation in the presence of a superacid. Journal of Organometallic Chemistry 2004, 689 (4) , 705-713. https://doi.org/10.1016/j.jorganchem.2003.11.029
  94. Andreas Franken, Neil J. Bullen, Tomáš Jelínek, Mark Thornton-Pett, Simon J. Teat, William Clegg, John D. Kennedy, Michaele J. Hardie. Structural chemistry of halogenated monocarbaboranes: the extended structures of Cs[1-HCB 9 H 4 Br 5 ], Cs[1-HCB 11 H 5 Cl 6 ] and Cs[1-HCB 11 H 5 Br 6 ]. New J. Chem. 2004, 28 (12) , 1499-1505. https://doi.org/10.1039/B410929E
  95. Nathan J. Patmore, Michael J. Ingleson, Mary F. Mahon, Andrew S. Weller. Investigation of the synthesis of {Mo(η 5 -C 5 H 5 )(CO) 3 } + fragments partnered with the monoanionic carboranes [closo-CB 11 H 11 Br] − , [closo-CB 11 H 6 Br 6 ] − and [closo-HCB 11 Me 11 ] − by silver salt metathesis and hydride abstraction. Dalton Trans. 2003, 93 (14) , 2894-2904. https://doi.org/10.1039/B303537A
  96. Chi-Wing Tsang, Qing-Chuan Yang, C. W. Thomas Mak, Zuo-Wei Xie. Synthesis and Structure of Solvated Protons Incorporating Weakly Coordinating Anions. Precursors of Superacids†. Chinese Journal of Chemistry 2002, 20 (11) , 1241-1248. https://doi.org/10.1002/cjoc.20020201116
  97. David M. Schubert. Boron Hydrides, Heteroboranes, and their Metalla Derivatives. 2002,,https://doi.org/10.1002/0471238961.0215181519030821.a01.pub2
  98. Michael Mormann, Dietmar Kuck. Synthesis of [1-13C]-para-xylene and [2-13C]-para-xylene. Journal of Labelled Compounds and Radiopharmaceuticals 2002, 45 (7) , 601-610. https://doi.org/10.1002/jlcr.584
  99. Zhengkun Yu, Andrey V. Korolev, Mary Jane Heeg, Charles H. Winter. Synthesis and structural characterization of complexes derived from treatment of gallium trichloride with 3,5-diphenylpyrazole. Polyhedron 2002, 21 (11) , 1117-1123. https://doi.org/10.1016/S0277-5387(02)00931-2
  100. Henk Buck. Calculated geometries and charge distributions of 4n and 4n + 2 ?-ring systems linked with ?CH2+: An asymmetric versus symmetric ?-delocalization. International Journal of Quantum Chemistry 2002, 89 (5) , 464-476. https://doi.org/10.1002/qua.10347
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