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Collect. Czech. Chem. Commun. 2002, 67, 1025-1034
https://doi.org/10.1135/cccc20021025

C-Halogenation of the closo-[CB11H12]- Anion

Zbyněk Janoušek, Cameron L. Hilton, Peter J. Schreiber and Josef Michl*

Department of Chemistry and Biochemistry, University of Colorado at Boulder, Boulder, CO 80309-0215, U.S.A.

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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>
  • Suponitsky Kyrill Yu., Anisimov Alexei A., Anufriev Sergey A., Sivaev Igor B., Bregadze Vladimir I.: 1,12-Diiodo-Ortho-Carborane: A Classic Textbook Example of the Dihalogen Bond. Crystals 2021, 11, 396. <https://doi.org/10.3390/cryst11040396>
  • Štíbr Bohumil: Alpha shift correlation (ASC) method. Sensitivity of 11B NMR shifts to halogen substitution in the ten-vertex nido and arachno series of boron clusters. Linear behavior of NMR effects. Inorganica Chimica Acta 2018, 471, 615. <https://doi.org/10.1016/j.ica.2017.11.040>
  • Hahn Nathan T., Seguin Trevor J., Lau Ka-Cheong, Liao Chen, Ingram Brian J., Persson Kristin A., Zavadil Kevin R.: Enhanced Stability of the Carba-closo-dodecaborate Anion for High-Voltage Battery Electrolytes through Rational Design. J. Am. Chem. Soc. 2018, 140, 11076. <https://doi.org/10.1021/jacs.8b05967>
  • Štíbr Bohumil, Tok Oleg L., Holub Josef: Quantitative Assessment of Substitution NMR Effects in the Model Series of o-Carborane Derivatives: α-Shift Correlation Method. Inorg. Chem. 2017, 56, 8334. <https://doi.org/10.1021/acs.inorgchem.7b01023>
  • Štíbr B.: 11B-NMR shielding effects in the closo borane series: sensitivity of shifts and their additivity. New J. Chem. 2017, 41, 14452. <https://doi.org/10.1039/C7NJ02689G>
  • Šembera Filip, Plutnar Jan, Higelin Alexander, Janoušek Zbyněk, Císařová Ivana, Michl Josef: Metal Complexes with Very Large Dipole Moments: the Anionic Carborane Nitriles 12-NC–CB11X11– (X = H, F, CH3) as Ligands on Pt(II) and Pd(II). Inorg. Chem. 2016, 55, 3797. <https://doi.org/10.1021/acs.inorgchem.5b02678>
  • 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>
  • Fete Matthew G., Havlas Zdeněk, Michl Josef: HCB11(CF3)nF11-n−: Inert Anions with High Anodic Oxidation Potentials. J. Am. Chem. Soc. 2011, 133, 4123. <https://doi.org/10.1021/ja111035k>
  • Valášek Michal, Štursa Jan, Pohl Radek, Michl Josef: Microwave-Assisted Alkylation of [CB11H12]− and Related Anions. Inorg. Chem. 2010, 49, 10247. <https://doi.org/10.1021/ic101234p>
  • Ringstrand Bryan, Bateman Devon, Shoemaker Richard K., Janoušek Zbyněk: Improved synthesis of [closo-1-CB9H10]– anion and new C-substituted derivatives. Collect. Czech. Chem. Commun. 2009, 74, 419. <https://doi.org/10.1135/cccc2008151>
  • Michl Josef: Chemistry of the three-dimensionally aromatic CB11 cage. Pure and Applied Chemistry 2008, 80, 429. <https://doi.org/10.1351/pac200880030429>
  • Vyakaranam Kamesh, Janoušek Zbyněk, Eriksson Ludvig, Michl Josef: Preparation of undecamethylated and hexamethylated 1‐halocarba‐closo‐dodecaborate anions. Heteroatom Chemistry 2006, 17, 217. <https://doi.org/10.1002/hc.20224>
  • 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>
  • Macháček Jan, Plešek Jaromír, Holub Josef, Hnyk Drahomír, Všetečka Václav, Císařová Ivana, Kaupp Martin, Štíbr Bohumil: New route to 1-thia-closo-dodecaborane(11), closo-1-SB11H11, and its halogenation reactions. The effect of the halogen on the dipole moments and the NMR spectra and the importance of spin–orbit coupling for the 11B chemical shifts. Dalton Trans. 2006, 1024. <https://doi.org/10.1039/B512345C>
  • Franken Andreas, Jelínek Tomáš, Taylor Richard G., Ormsby Daniel L., Kilner Colin A., Clegg William, Kennedy John D.: Polyhedral monocarbaborane chemistry. Some C-phenylated seven, eight, nine, ten, eleven and twelve-vertex species. Dalton Trans. 2006, 5753. <https://doi.org/10.1039/B609908D>
  • Holub Josef, Bakardjiev Mario, Štíbr Bohumil: The Synthesis of 10-Halo-Substituted Derivatives of nido-7,8,9-PC2B8H11 and [nido-7,8,9-PC2B8H10]- and New Linear Correlations Between NMR Parameters. Collect. Czech. Chem. Commun. 2005, 70, 1861. <https://doi.org/10.1135/cccc20051861>
  • Vyakaranam Kamesh, Körbe Stefanie, Divišová Hana, Michl Josef: A New Type of Intermediate, C+(BCH3)11- ↔ C(BCH3)11, in a Grob Fragmentation Coupled with Intramolecular Hydride Transfer. A Nonclassical Carbocation Ylide or a Carbenoid?. J. Am. Chem. Soc. 2004, 126, 15795. <https://doi.org/10.1021/ja0466558>
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