Electrophilic methylation of the closo-1,10-R2C2B8H8 (1) (R = H or Me) dicarbaboranes at higher temperatures or thermal rearrangement of the 1,6-R2C2B8Me8 (3) compounds at 400-500 °C generated the B-permethylated derivatives closo-1,10-R2C2B8Me8 (2) in quantitative (>95%) yields. The compounds exhibit extreme air stability as a consequence of a rigid, egg shaped hydrocarbon structures incorporating inner 1,10-C2B8 carborane core.

Department of General and Inorganic Chemistry Faculty of Chemical Technology University of Pardubice Studentská 573 532 10 Pardubice Czech Republic

Institute of Inorganic Chemistry Academy of Sciences of the Czech Republic Husinec Řež 1001 Czech Republic

Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences Flemingovo nám 2 166 10 Prague 6 Czech Republic

Zobrazit více v PubMed

For review, see: Grimes R. N., Carboranes, Academic Press, 3rd edn, 2016

Garrett P. M. Smart J. C. Hawthorne M. F. J. Am. Chem. Soc. 1969;91:4707–4710. doi: 10.1021/ja01045a021. DOI

Owen D. A. Smart J. C. Garrett P. M. Hawthorne M. F. J. Am. Chem. Soc. 1971;93:1362–1368. doi: 10.1021/ja00735a008. DOI

Wedge T. J. Herzog A. Huertas R. Lee M. W. Knobler C. B. Hawthorne M. F. Organometallics. 2004;23:482–489. doi: 10.1021/om030514h. DOI

Getman T. D. Garrett P. M. Knobler C. B. Hawthorne M. F. Thorne K. MacKenzie J. D. Organometallics. 1992;11:2723–2725. doi: 10.1021/om00043a072. DOI

Bakardjiev M. Štíbr B. Holub J. Padělková Z. Růžička A. Organometallics. 2015;34:450–454. doi: 10.1021/om500988z. DOI

Rockwell J. J. Herzog A. Peymann T. Knobler C. B. Hawthorne M. F. Curr. Sci. 2000;78:405.

Körbe S. Schreiber P. J. Michl J. Chem. Rev. 2006;106:5208–5249. doi: 10.1021/cr050548u. PubMed DOI

Douvris C. Michl J. Chem. Rev. 2013;113:PR179–PR233. doi: 10.1021/cr400059k. PubMed DOI

Jiang W. Knobler C. B. Mortimer M. D. Hawthorne M. F. Angew. Chem., Int. Ed. 1995;34:1332. doi: 10.1002/anie.199513321. DOI

Bakardjiev M. Tok O. L. Růžička A. Růžičková Z. Holub J. Špalt Z. Štíbr B. Dalton Trans. 2018;47:11070–11076. doi: 10.1039/C8DT02586J. PubMed DOI

Bakardjiev M. Štíbr B. Holub J. Tok O. L. Švec P. Růžičková Z. Růžička A. Inorg. Chem. 2016;55:7068–7074. doi: 10.1021/acs.inorgchem.6b00964. PubMed DOI

Štíbr B. Plešek J. Heřmánek S. Collect. Czech. Chem. Commun. 1973;38:338. doi: 10.1135/cccc19730338. DOI

Fanfrlík J. Lepšík M. Hořínek D. Havlas Z. Hobza P. ChemPhysChem. 2006;7:1100. doi: 10.1002/cphc.200500648. PubMed DOI

Esterhuysen C. Hesselmann A. Clark T. ChemPhysChem. 2017;18:1. doi: 10.1002/cphc.201700027. PubMed DOI

Fanfrlík J. Pecina A. Řezáč J. Sedlák R. Hnyk D. Lepšík M. Hobza P. Phys. Chem. Chem. Phys. 2017;19:18194. doi: 10.1039/C7CP02762A. PubMed DOI

Melichar P. Hnyk D. Fanfrlík J. A systematic examination of classical and multi-center bonding in heteroborane clusters. Phys. Chem. Chem. Phys. 2018;20:4666–4675. doi: 10.1039/C7CP07422K. PubMed DOI

Hnyk D. Všetečka V. Drož L. Exner O. Charge Distribution Within 1,2-Dicarba-closo-dodecaborane: Dipole Moments of Its Phenyl Derivatives. Collect. Czech. Chem. Commun. 2001;66:1375–1379. doi: 10.1039/C7CP07422K. PubMed DOI

Teixidor F. Barberà G. Vaca A. Kivekäs R. Sillanpää R. Oliva J. Viñas C. J. Am. Chem. Soc. 2005;127:10158–10159. doi: 10.1021/ja052981r. PubMed DOI

Hutton W. C. Venable T. L. Grimes R. N. J. Am. Chem. Soc. 1984;106:29–37. doi: 10.1021/ja00313a007. DOI

McFarlane W. A. Proc. R. Soc. London, Ser. A. 1968;306:175–199. doi: 10.1098/rspa.1968.0145. DOI

Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Scalmani G., Barone V., Mennucci B., Petersson G. A., Nakatsuji H., Caricato M., Li X., Hratchian H. P., Izmaylov A. F., Bloino J., Zheng G., Sonnenberg J. L., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery Jr J. A., Peralta J. E., Ogliaro F., Bearpark M., Heyd J. J., Brothers E., Kudin K. N., Staroverov V. N., Kobayashi R., Normand J., Raghavachari K., Rendell A., Burant J. C., Iyengar S. S., Tomasi J., Cossi M., Rega N., Millam J. M., Klene M., Knox J. E., Cross J. B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R. E., Yazyev O., Austin A. J., Cammi R., Pomelli C., Ochterski J. W., Martin R. L., Morokuma K., Zakrzewski V. G., Voth G. A., Salvador P., Dannenberg J. J., Dapprich S., Daniels A. D., Farkas Ö., Foresman J. B., Ortiz J. V., Cioslowski J. and Fox D. J., Gaussian, Inc., Wallingford CT, 2009

Flükiger P., Lüthi H. P., Portmann S. and Weber J., MOLEKEL 4.3, Swiss Center for Scientific Computing, Manno (Switzerland), 2000

Portmann S. and Lüthi H. P., MOLEKEL: CHIMIA, 2007, Vol. 28, p. 555

Riley K. E. Tran K.-A. Lane P. Murray J. S. Politzer P. J Comput Sci. 2016;17:273. doi: 10.1016/j.jocs.2016.03.010. DOI

Sheldrick G. M. Acta Crystallogr., Sect. C: Struct. Chem. 2015;A71:3–8. PubMed PMC

Poater J. Sola M. Viñas C. Teixidor F. Angew. Chem., Int. Ed. 2014;53:12191–12195. doi: 10.1002/anie.201407359. PubMed DOI

Poater J. Sola M. Viñas C. Teixidor F. Chem.–Eur. J. 2016;22:7437–7443. doi: 10.1002/chem.201600510. PubMed DOI

Carbon-Substituted Amines of the Cobalt Bis(dicarbollide) Ion: Stereochemistry and Acid-Base Properties