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Collect. Czech. Chem. Commun. 1981, 46, 1748-1763
https://doi.org/10.1135/cccc19811748

Synthesis of B-alkyl derivatives of o-carborane by alkylation under electrophilic conditions; Scope and limitation

Jaromír Plešek, Zbyněk Plzák, Jiří Stuchlík and Stanislav Heřmánek

Institute of Inorganic Chemistry, Czechoslovak Academy of Sciences, 250 68 Řež

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  • Wang Lingyao, Jiang Yunjia, Duttwyler Simon, Lin Furong, Zhang Yuanbin: Chemistry of three-dimensional icosahedral boron clusters anions: closo-dodecaborate (2-) [B12H12]2- and carba-closo-dodecaborate(-) [CB11H12]-. Coordination Chemistry Reviews 2024, 516, 215974. <https://doi.org/10.1016/j.ccr.2024.215974>
  • Shernyukov Andrey V., Salnikov George E., Rudakov Dmitry A., Genaev Alexander M.: Noncatalytic Bromination of Icosahedral Dicarboranes: The Key Role of Anionic Bromine Clusters Facilitating Br Atom Insertion into the B–H σ-Bond. Inorg. Chem. 2021, 60, 3106. <https://doi.org/10.1021/acs.inorgchem.0c03392>
  • Cao Ke, Zhang Cai-Yan, Xu Tao-Tao, Wu Ji, Ding Li-Fang, Jiang Linhai, Yang Junxiao: Palladium catalyzed/counter ion tuned selective methylation of o-carboranes. Journal of Organometallic Chemistry 2019, 902, 120956. <https://doi.org/10.1016/j.jorganchem.2019.120956>
  • Tang Cen, Zhang Jiji, Zhang Jie, Xie Zuowei: Regioselective Nucleophilic Alkylation/Arylation of B–H Bonds in o-Carboranes: An Alternative Method for Selective Cage Boron Functionalization. J. Am. Chem. Soc. 2018, 140, 16423. <https://doi.org/10.1021/jacs.8b10270>
  • Kaleta Jiří, Akdag Akin, Crespo Raül, Piqueras Mari‐Carmen, Michl Josef: Evidence for an Intermediate in the Methylation of CB11H12− with Methyl Triflate: Comparison of Electrophilic Substitution in Cage Boranes and in Arenes. ChemPlusChem 2013, 78, 1174. <https://doi.org/10.1002/cplu.201300219>
  • Douvris Christos, Michl Josef: Update 1 of: Chemistry of the Carba-closo-dodecaborate(−) Anion, CB11H12–. Chem. Rev. 2013, 113, PR179. <https://doi.org/10.1021/cr400059k>
  • Olid David, Núñez Rosario, Viñas Clara, Teixidor Francesc: Methods to produce B–C, B–P, B–N and B–S bonds in boron clusters. Chem. Soc. Rev. 2013, 42, 3318. <https://doi.org/10.1039/c2cs35441a>
  • Zhizhin K. Yu., Zhdanov A. P., Kuznetsov N. T.: Derivatives of closo-decaborate anion [B10H10]2− with exo-polyhedral substituents. Russ. J. Inorg. Chem. 2010, 55, 2089. <https://doi.org/10.1134/S0036023610140019>
  • Kalinin V. N., Ol’shevskaya V. A.: Some aspects of the chemical behavior of icosahedral carboranes. Russ Chem Bull 2008, 57, 815. <https://doi.org/10.1007/s11172-008-0120-x>
  • Vyakaranam Kamesh, Havlas Zdenek, Michl Josef: Aromatic Substitution with Hypercloso C(BCH3)11:  A New Mechanism. J. Am. Chem. Soc. 2007, 129, 4172. <https://doi.org/10.1021/ja066520x>
  • Körbe Stefanie, Schreiber Peter J., Michl Josef: Chemistry of the Carba-closo-dodecaborate(−) Anion, CB11H12-. Chem. Rev. 2006, 106, 5208. <https://doi.org/10.1021/cr050548u>
  • Teixidor Francesc, Barberà Gemma, Viñas Clara, Sillanpää Reijo, Kivekäs Raikko: Synthesis of Boron-Iodinated o-Carborane Derivatives. Water Stability of the Periodinated Monoprotic Salt. Inorg. Chem. 2006, 45, 3496. <https://doi.org/10.1021/ic060124y>
  • Teixidor Francesc, Barberà Gemma, Vaca Albert, Kivekäs Raikko, Sillanpää Reijo, Oliva Josep, Viñas Clara: Are Methyl Groups Electron-Donating or Electron-Withdrawing in Boron Clusters? Permethylation of o-Carborane. J. Am. Chem. Soc. 2005, 127, 10158. <https://doi.org/10.1021/ja052981r>
  • Zharov Ilya, Weng Tsu-Chien, Orendt Anita M., Barich Dewey H., Penner-Hahn James, Grant David M., Havlas Zdenek, Michl Josef: Metal Cation−Methyl Interactions in CB11Me12- Salts of Me3Ge+, Me3Sn+, and Me3Pb+. J. Am. Chem. Soc. 2004, 126, 12033. <https://doi.org/10.1021/ja0475205>
  • Jiang Wei, Knobler Carolyn B., Hawthorne M. Frederick: Decakis(dichlormethyl)‐1, 12‐dicarba‐closo‐dodecaboran(12): Tarnung eines ikosaedrischen Carborans mit sperrigen funktionellen Substituenten. Angewandte Chemie 1996, 108, 2653. <https://doi.org/10.1002/ange.19961082115>
  • Jiang Wei, Knobler Carolyn B., Hawthorne M. Frederick: Decakis(dichloromethyl)‐1,12‐dicarba‐closo‐dodecaborane(12): Camouflage of an Icosahedral Carborane by Using Bulky Functional Substituents. Angew. Chem. Int. Ed. Engl. 1996, 35, 2536. <https://doi.org/10.1002/anie.199625361>
  • Lomme Petra, Roth Martin, Englert Ulli, Paetzold Peter: Electrophilic Substitution at the NB9 and NB11closo‐Skeletons. Chem. Ber. 1996, 129, 1227. <https://doi.org/10.1002/cber.19961291014>
  • Zakharkin L. L, Ol'shevskaya V. A., Vorontsov E. V., Petrovsky P. V.: Synthesis of mono-, di-, tri-, and tetraethyl-o-carboranes by electrophilic alkylation ofo-carborane with ethyl bromide in the presence of AICl3 and their transformations. Russ Chem Bull 1996, 45, 2614. <https://doi.org/10.1007/BF01431128>
  • Zheng Zhiping, Knobler Carolyn B., Mortimer Mark D., Kong Gapgoung, Hawthorne M. Frederick: Hydrocarbon-Soluble Mercuracarborands:  Syntheses, Halide Complexes, and Supramolecular Chemistry. Inorg. Chem. 1996, 35, 1235. <https://doi.org/10.1021/ic951069o>
  • King Benjamin T., Janoušek Zbyněk, Grüner Bohumír, Trammell Matthew, Noll Bruce C., Michl Josef: Dodecamethylcarba-closo-dodecaborate(−) Anion, CB11Me12-. J. Am. Chem. Soc. 1996, 118, 3313. <https://doi.org/10.1021/ja9541443>
  • Jiang Wei, Knobler Carolyn B., Mortimer Mark D., Hawthorne M. Frederick: Ein getarntes ikosaedrisches Carboran: Dodecamethyl‐1,12‐dicarba‐closo‐dodecaboran(12) und verwandte Verbindungen. Angewandte Chemie 1995, 107, 1470. <https://doi.org/10.1002/ange.19951071222>
  • Jiang Wei, Knobler Carolyn B., Mortimer Mark D., Hawthorne M. Frederick: A Camouflaged Icosahedral Carborane: Dodecamethyl‐1,12‐dicarba‐closo‐dodecaborane(12) and Related Compounds. Angew. Chem. Int. Ed. Engl. 1995, 34, 1332. <https://doi.org/10.1002/anie.199513321>
  • Zakharkin L. I., Ol'shevskaya V. A.: Synthesis of 9-benzyl-o- and 9-benzyl-m-carboranes containing functional substituents in the benzene ring by electrophilic alkylation ofo- andm-carboranes by the correspondingR-benzyl halides. Russ Chem Bull 1995, 44, 1099. <https://doi.org/10.1007/BF00707061>
  • Bonnetot B., Aboukhassib A., Mongeot H.: Study of the interaction of AlCl3 with the B10H102− cage in the solid state. Inorg Chim Ada 1989, 156, 183. <https://doi.org/10.1016/S0020-1693(00)83498-2>
  • Vondrák Tomáš, Plešek Jaromír, Heřmánek Stanislav, Štíbr Bohumil: Charge distribution in icosahedral carboranes: A UV photoelectron spectroscopic study. J Polyhedron 1989, 8, 805. <https://doi.org/10.1016/S0277-5387(00)83850-4>
  • Zakharkin L. I., Ol'shevskaya V. A., Anikina E. V.: Electrophilic alkylation of o-and m-carboranes by 4-chlorobutyric acid and 5-chlorovaleric acid in the presence of AlCl3. Russ Chem Bull 1987, 36, 795. <https://doi.org/10.1007/BF00962323>
  • Zakharkin L. I., Kovredov A. I., Ol'shevskaya V. A., Vitt C. V.: Formation of B-n-propyl-o- and m-carboranes by electrophilic alkylation of o- and m-carboranes with isopropyl halides and isomerization of 9-isopropyl-o- and m-carboranes in the presence of AlCl3. Russ Chem Bull 1983, 32, 1528. <https://doi.org/10.1007/BF00954380>