Studies on synthesis of boron and carborane cage derivatives

Yıl 2020, , 1 - 11, 29.03.2020

Sevban Doğan Akın Akdağ

https://doi.org/10.30728/boron.641589

Cited By: 1

Öz

Weakly coordinating anions are extremely versatile species for capturing and characterizing cationic intermediates. Among these anions, carboranes and some boranes are known to be the most weakly coordinating anions. In this study, the carboranes and boranes were synthesized in order to use in different fields. B₁₁H₁₄- was synthesized from NaBH4 and used to synthesize CB₁₁H₁₂-. CB₁₁H₁₂- was synthesized by carbene addition to undecaborate. B₁₁H₁₄- was converted to B₁₀H₁₄ by oxidation and extrusion of one boron vertex. CB11H12- was methylated on boron vertex to get HCB₁₁Me₁₁-. The methylated carborane cages are more hydrophobic and weakly coordinating anions. 

Anahtar Kelimeler

Borane, Carborane, Decaborane, Dodecacarborane, Undecaboran

Proje Numarası

2018-30-06-30-004

Kaynakça

• [1] Katchem spol, s. r. o. http://www.katchem.cz/en/ (accessed May 29, 2018).
• [2] Grimes R. N. Introduction and History, In Carboranes; Birtcher, K., Ed.; Fedor, John: United Kingdom, 1–5, 2016.
• [3] Sivaev I. B., Nitrogen heterocyclic salts of polyhedral borane anions: From ionic liquids to energetic materials, Chem. Heterocycl. Compd., 53 (6–7), 638–658, 2017.
• [4] Schroeder M. A., Possible chemical mechanisms for boron hydride acceleration of nitramine decomposition: Literature review, J. Propuls. Power, 14 (6), 981–990, 1998.
• [5] Johnson J. W., Lithium closoboranes as electrolytes in solid cathode lithium cells, J. Electrochem. Soc., 127 (7), 1653, 1980.
• [6] Johnson J. W., Lithium closoboranes II. stable nonaqueous electrolytes for elevated temperature lithium cells, J. Electrochem. Soc., 128 (4), 932, 1981.
• [7] Johnson J. W., Lithium closoborane electrolytes, J. Electrochem. Soc., 129 (10), 2213–2219, 1982.
• [8] Hertler W. R., Raasch M. S., Chemistry of boranes, XIV. Amination of B10H10-2 and B12H12-2 with hydroxylamine-O-sulfonic acid, Inorg. Chem., 86 (11), 3661–3668, 1964.
• [9] Kaszynski P., Douglass, A. G., Organic derivatives of closo-boranes: A new class of liquid crystal materials, J. Organomet. Chem. 581 (1–2), 28–38, 1999.
• [10] Fibbioli M., Berger M., Schmidtchen F. P., Pretsch E., Polymeric membrane electrodes for monohydrogen phosphate and sulfate, Anal. Chem., 72 (1), 156–160, 2000.
• [11] Gruner B., Bonnetot B., Mongeot H., Synthesis of N- and B-substituted derivatives of closo-amino-undecahydro-dodecaborate(1-) anion, Collect. Czech. Chem. Commun., 62, 1185–1204, 1997.
• [12] Bernard R., Cornu D., Grüner B., Dozol J. F., Miele P., Bonnetot B., Synthesis of [B12H12]2- based extractants and their application for the treatment of nuclear wastes, J. Organomet. Chem., 657, 83–90, 2002.
• [13] Nedunchezhian K., Aswath N., Thıruppathy M., Thirugnanamurthy S., Boron neutron capture therapy - A literature review, J. Clin. Diagnostic Res. 10 (12), 1–4, 2016.
• [14] Hawthorne M. F., The role of chemistry in the development of boron neutron capture therapy of cancer, Angew. Chem. Int. Ed. Engl., 32, 950–984, 1993.
• [15] Tolmachev B. V., Bruskin A., Sivaev I., Lundqvist H., Sjöberg S., Radiobromination of closo -dodecaborate anion. Aspects of labelling chemistry in aqueous solution using chloramine-T, Radiochim. Acta, 90, 229–235, 2002.
• [16] Grainger R. G., Hon F. R. A. C. R., Hon F. A. C. R., Intravascular contrast media—the past, the present and the future, Br. J. Radiol., 55 (649), 1–18, 1982.
• [17] Wilbur W. D. S., Iodinated borane cage molecules as x-ray contrast media WO9505202, 1995.
• [18] Dominique M., Spielvogel B., Contrast agents and compositions for radiological ımaging, and radiological ımaging method utilizing same, WO9308122, 1993.
• [19] Atkins P., Overton T., Rourke J., Weller M., Armstong F., The Group 13 Elements, In Inorganic Chemistry; Oxford University Press: Oxford, pp 325–334, 2009.
• [20] CRC Handbook of Chemistry and Physics; Lide, D. R., Ed.; CRC Press: Boca Raton, FL, 2005.
• [21] Hoffmann R., Lipscomb W. N., Theory of polyhedral molecules, III. population analyses and reactivities for the carboranes, J. Chem. Phys., 36 (12), 3489, 1962.
• [22] Stock A., Kuss E., Borwasserstoffe und die eihfachsten borhydride, Ber, 56, 789–808, 1923.
• [23] Heying T. L., Ager J. W., Clark S. L., Mangold D. J., Goldstein H. L., Hillman M., Polak R. J., Szymanski J. W., A new series of organoboranes, I. carboranes from the reaction of decaborane with acetylenic compounds, Inorg, Chem., 2 (6), 1089–1092, 1963.
• [24] Schroeder H., Heying T. L., Reiner J. R., A new series of organoboranes, II. The chlorination of 1,2-dicarbaclovododecaborane(12), Inorg. Chem., 2 (6), 1092–1096, 1963.
• [25] Grafstein D., Bobinski J., Dvorak J., Smith, H., Schwartz N., Cohen M. S., Fein M. M., Carboranes, III. reactions of the carboranes, Inorg. Chem., 2 (6), 1120–1125, 1963.
• [26] Alexander R. P., Schroeder H., Chemistry of decaborane-phosphorus compounds, IV. monomeric, oligomeric, and cyclic phosphinocarboranes, Inorg. Chem., 2 (6), 1107–1110, 1963.
• [27] Schroedbr H., Vickers G. D., The structure of neocarborane, Inorg. Chem. 2 (6), 1317–1319, 1963.
• [28] Fein M. M., Grafstein D., Paustian J. E., Bobinski J., Lichstein B. M., Mayes N., Schwartz N. N., Cohen, M. S., Carboranes, II. The preparation of 1- and 1,2-substituted carboranes, Inorg. Chem., 2 (6), 1115–1119, 1963.
• [29] Fein M. M., Bobinski J., Mayes N., Schwartz N., Cohen M. S., Carboranes, I. The preparation and chemistry of 1-ısopropenylcarborane and ıts derivatives (a new family of stable clovoboranes), Inorg. Chem., 2 (6), 1111–1115, 1963.
• [30] Grafstein D., Bobinsk, J., Dvorak J., Paustian J. E., Smith H. F., Karlan S., Vogel C., Fein M. M., Carboranes, IV. chemistry of bis-(1-carboranylalkyl) ethers, Inorg. Chem., 2 (6), 1125–1128, 1963.
• [31] Papetti S., Heying T. L., A New Series of Organoboranes, IV. The participation of the 1,2-dicarbaclovododecaborane(12) nucleus in some novel heteratomic ring systems, Inorg. Chem. 2 (6), 1105–1107, 1963.
• [32] Grafstein D., Dvorak J., Neocarboranes, a new family of stable organoboranes ısomeric with the carboranes, Inorg. Chem., 2 (6), 1128–1133, 1963.
• [33] Heying T. L., Ager J. W., Clark S. L., Alexander R. P., Papetti S., Reid J. A., Trotz S. I., A new series of organoboranes. ııı. some reactions of 1,2-dicarbaclovododecaborane(12) and Its derivatives, Inorg. Chem., 2 (6), 1097–1105, 1963.
• [34] Pitochelli A. R., Hawthorne M. F., The isolation of the icosahedral B12H12-2 ion, J. Am. Chem. Soc., 82, 3228, 1960.
• [35] Cyvin B. N., Brunvoll J., Cyvin S. J., Normal coordinate analysis of the dodecaborane ion, Spectrosc. Lett., 17 (9), 569–577, 1984.
• [36] Muetterties E. L., Chemistry of boranes, VI. preparation and structure of Bl0H14-2, Inorg. Chem., 2 (3), 647–648, 1963.
• [37] Knoth W. H., 1-B9H9CH- and B11H11CH-, J. Am. Chem. Soc., 89 (5), 1274–1275, 1967.
• [38] Plesek J., Jelinek T., Drdakova E., Hermanek S., A convenient preparation of 1-CB11H12- and its C-amino derivatives, Collect. Czechoslov. Chem. Commun., 49, 1559–1562, 1983.
• [39] Quintana W., Sneddon L. G., Synthesis and structural characterization of new boron-substituted monocarbon carborane adducts: Nido-8-L-7-CB10H12 (L = SMe2, PPh3), Inorg. Chem., 29 (17), 3242–3245, 1990.
• [40] Batsanov A. S., Fox M. A., Goeta A. E., Howard J. A. K., Hughes A. K., Malget J. M., A convenient cyanide-free “One-Pot” synthesis of Nido-Me3N-7-CB10H12 and Nido-7-CB10H13−. J. Chem. Soc. Dalt. Trans., No. 13, 2624, 2002.
• [41] Franken A., Bullen N. J., Jelinek T., Thornton-Pett M., Teat S. J., Clegg W., Kennedy J. D., Hardie M. J., Structural chemistry of halogenated monocarbaboranes: The extended structures of Cs[1-HCB9H4Br5], Cs[1-HCB11H5Cl6] and Cs[1-HCB11H5Br6], New J . Chem., 28, 1499–1505, 2004.
• [42] Franken A., King B. T., Rudolph J., Rao P., Noll B. C., Michl J., Preperation of [Closo -CB11H12 ] – by dichloro carbene insertion into [Nido-B11H14]–, Collect. Czech. Chem. Commun., 66, 1238–1249, 2001.
• [43] Rempala P., Michl J., A proposed mechanism of [Closo-CB11H12]– formation by dichlorocarbene Insertion into [Nido-B11H14]–. A computational study by density functional Theory, Collect. Czech. Chem. Commun., 68, 644–662, 2003.
• [44] Zhang J., Chan H., Xie, Z., Reaction of 13-vertex carboranes with nucleophiles : Unprecedented cage-carbon extrusion and formation of monocarba-closo-dodecaborate dnions **, Angew. Chem. Int. Ed., 47, 9447–9449, 2008.
• [45] Jelinek T., Plesek J., Mares F., Hermanek S., Stibr B., Some electrophilic substitution reaction of closo-[1-CB11H12J- and one-boron insertion into Nido- 7-L-7-CB10H12 (L = H- or Me3N) Compounds, isolation of all three B-substituted closo-Me3N-1-CB11H11 derivatives, Polyhedron, 6 (11), 1981–1986, 1987.
• [46] Finze M., Carbon extrusion/cluster contraction: Synthesis of the fluorinated cyano-closo-undecaborate K2 [3-NC-Closo-B11 F10 ]**, Angew. Chem. Int. Ed., 46, 8880–8882, 2007.
• [47] Zhang J., Zheng F., Chan H., Xie Z., Reaction of a 14-vertex carborane with nucleophiles: Formation of nido -C2B2, Nido-C2B11, and Closo-CB11 carborane anions, Inorg. Chem., 48, 9786–9791, 2009.
• [48] Dunks G. B., Ordonez K. P. A., One-step synthesis of B11H14-ion from NaBH4, Inorg. Chem. 17 (6), 1514–1516, 1978.
• [49] Geis V., Guttsche K., Knapp C., Scherer H., Uzun, R., Synthesis and characterization of synthetically useful salts of the weakly-coordinating dianion [B12Cl12]2-. Dalt. Trans. 15, 2687–2694, 2009.
• [50] Dunks G. B., Palmer-Ordonez, K., Hedaya E., Decaborane(14), Inorg. Synth., 22, 202–207, 1983.
• [51] Hill W. H., Merrill J. M., Russell H. L., Hill D. L., Heacock J. F., Colorimetric determination of boron hydrides by means of phosphomolybdic acid, Am. Ind. Hyg. Assoc. J., 20 (1), 5–12, 1959.
• [52] Pérez S., Sanz Miguel P. J., Macías R., Decaborane anion tautomerism: Ion pairing and proton transfer control, Dalt. Trans., 47 (16), 5850–5859, 2018.
• [53] King B. T., Methylated and trifiuoromethylated CB11 clusters, University of Colorado, 2000.