Abstract
The reactions of fullerene C60 with isocyanurate-substituted azides afforded individual regioisomers of bis-adducts. The structures of the regioisomers depend on the structure of the organic fragment in azide and are determined primarily by the bulkiness of this fragment.
Similar content being viewed by others
References
A Hirsch and M. Brettreich, Fullerenes: Chemistry and Reactions, Wiley-VCH Verlag, Wienheim, 2005, 422 pp.
L. N. Sidorov, M A. Yurovskaya, A. Ya. Borshchevskii, I. V. Trushkov, and I. N. Ioffe, Fullereny [Fullerenes], Ekzamen, Moscow, 2004, 688 pp. (in Russian).
R. Taxylor, Lecture Notes on Fullerene Chemistry: a Handbook for Chemists, Imperial College Press, London, 1999, 268 pp.
Y. Nakamura, K. Okawa, and M. Matsumoto, Tetrahedron, 2000, 56, 5429.
J.-F. Nierengarten, J.-F. Eckert, D. Felder, J.-F. Nicoud, N. Armaroli, G. Marconi, V. Vicinelli, C. Boudon, J.-P. Gisselbrecht, M. Gross, G. Hadziioannou, V. Krasnikov, L. Ouali, L. Echegoyen, and S.-G. Liu, Carbon, 2000, 38, 1587.
P. M. Smith, A. L. McCarty, N. Y. Nguyen, M. E. Zandler, and F. D’Souza, J. Chem. Soc., Chem. Commun., 2003, 1754.
T. Da Ros and M. Prato, J. Chem. Soc., Chem. Commun., 2003, 663.
D. L. Kepert and B. W. Clare, Coord. Chem. Rev., 1996, 155, 1.
Y. Ishida, H. Ito, D. Mori, and K. Saigo, Tetrahedron Lett., 2005, 46, 109.
T. Grösser, M. Prato, V. Lucchini, A. Hirsch, and F. Wudl, Angew. Chem., 1995, 107, 1462 [Angew. Chem., Int. Ed. Engl., 1995, 34, 1343].
I. P. Romanova, G. G. Yusupova, A. A. Nafikova, V. I. Kovalenko, and O. G. Sinyashin, Izv. Akad. Nauk, Ser. Khim., 2002, 1376 [Russ. Chem. Bull., Int. Ed., 2002, 51, 1491].
O. G. Sinyashin, I. P. Romanova, G. G. Yusupova, V. I. Kovalenko, V. V. Yanilkin, and N. M. Azancheev, Mendeleev Commun., 2000, 96.
O. G. Sinyashin, I. P. Romanova, G. G. Yusupova, S. G. Fattakhov, A. A. Nafikova, V. I. Kovalenko, N. M. Azancheev, and V. S. Reznik, Izv. Akad. Nauk, Ser. Khim., 2001, 2064 [Russ. Chem. Bull., Int. Ed., 2001, 50, 2063].
A. Hirsch and B. Nuber, Acc. Chem. Res., 1999, 32, 795.
O. G. Sinyashin, I. P. Romanova, F. R. Sagitova, V. A. Pavlov, V. I. Kovalenko, Y. V. Badeev, N. M. Azancheev, A. V. Ilyasov, A. V. Chernova, and I. I. Vandyukova, Mendeleev Commun., 1998, 78.
G. Schick, A. Hirsch, H. Mauser, and T. Clark, Chem. Eur. J., 1996, 2, 935.
G.-X. Dong, J.-S. Li, and T.-H. Chan, J. Chem. Soc., Chem. Commun., 1995, 1725.
P. P. Kanakamma, S.-L. Huang, C.-G. Juo, G.-R. Her, and T.-Y. Luh, Chem. Eur. J., 1998, 4, 2037.
L.-L. Shiu, K.-M. Chien, T.-Y. Li, G.-R. Her, and T.-Y. Luh, J. Chem. Soc., Chem. Commun., 1995, 1159.
J. P. Perdew, K. Burke, and M. Ernzerhof, Phys. Rev. Lett., 1996, 77, 3865.
D. N. Laikov, Chem. Phys. Lett., 1997, 281, 151.
F. Cardullo, L. Isaacs, F. Diederich, J.-P. Gisselbrecht, C. Boudon, and M. Gross, J. Chem. Soc., Chem. Commun., 1996, 797.
C. Boudon, J.-P. Cisselbrecht, M. Gross, L. Isaacs, H. L. Anderson, R. Faust, and F. Diederich, Helv. Chim. Acta, 1995, 78, 1334.
A. E. Derome, Modern NMR Techniques for Chemistry Research, Pergamon, Oxford, 1988, 280 pp.
Atta-ur-Rahman, One and Two Dimensional NMR Spectroscopy, Elsevier, Amsterdam, 1989, 579.
Author information
Authors and Affiliations
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 672–677, April, 2006.
Rights and permissions
About this article
Cite this article
Romanova, I.P., Yusupova, G.G., Larionova, O.A. et al. Synthesis and electrochemical properties of individual isomers of isocyanurate-substituted bis-organodiazadihomofullerenes. Russ Chem Bull 55, 697–702 (2006). https://doi.org/10.1007/s11172-006-0315-y
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/s11172-006-0315-y