Conclusions
-
1.
The reaction of phenyl-(9-m-carboranyl)bromonium borofluoride with nucleophiles is less regioselective than the analogous reactions of phenyl-(9-m-carboranyl)iodonium salts, and is more often accompanied by disruption of the carborane ring.
-
2.
With the symmetrical bis(9-m-carboranyl)bromonium salts, both nucleophilic substitution and radical reactions proceed with much more difficulty than with the phenyl-(B-carboranyl) halonium and diphenylhalonium compounds.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
V. V. Grushin, T. P. Tolstaya, and I. N. Lisichkina, Izv. Akad. Nauk SSSR, Ser. Khim., 2412 (1982).
G. A. Olah, Halonium Ions, New York (1975).
O. A. Reutov, L. G. Makarova, and T. P. Tolstaya, Zh. Org. Khim.,5, 1521 (1969).
A. N. Nesmeyanov, T. P. Tolstaya, and L. S. Isaeva, Dokl. Akad. Nauk SSSR,117, 996 (1957).
V. V. Grushin, T. P. Tolstaya, I. N. Lisichkina, and A. N. Vanchikov, Dokl. Akad. Nauk SSSR,264, 868 (1982).
V. V. Grushin, Dissertation, Moscow (1984).
V. V. Grushin, T. P. Tolstaya, and I. N. Lisichkina, Izv. Akad. Nauk SSSR, Ser. Khim., 2633 (1982).
V. V. Grushin, T. P. Tolstaya, and I. N. Lisichkina, Izv. Akad. Nauk SSSR, Ser. Khim., 2165 (1983).
V. V. Grushin, T. P. Tolstaya, I. N. Lisichkina, Yu. K. Grishin, T. M. Shcherbina, V. Ts. Kampel', V. I. Bregadze, and N. N. Godovikov, Izv. Akad. Nauk SSSR, Ser. Khim., 472 (1983).
V. V. Grushin, T. P. Tolstaya, A. I. Yanovskii, and Yu. T. Strichkov, Izv. Akad. Nauk SSSR, Ser. Khim., 855 (1984).
D. V. Howe, C. J. Jones, R. J. Wiersema, and M: F. Hawthorne, Inorg. Chem.,10, 2516 (1971).
A. N. Nesmeyanov and L. G. Makarova, Scientific Proceedings, Moscow State University [in Russian], Moscow (1950), No. 132, Book 7, p. 109.
O. A. Ptitsina, M. E. Gurskii, and O. A. Reutov, Zh. Org. Khim.,10, 2246 (1974).
O. A. Ptitsyna, M. E. Pudeeva, and O. A. Reutov, Dokl. Akad. Nauk SSSR,165, 838 (1965).
A. N. Nesmeyanov, O. A. Reutov, T. P. Tolstaya, O. A. Ptitsyna, L. S. Isaeva, M. F. Turchinskii, and G. P. Bochkareva, Dokl. Akad. Nauk SSSR,125, 1265 (1959).
O. A. Ptitsyna, T. V. Levashova, K. P. Butin, and O. A. Reutov, Dokl. Akad. Nauk SSSR,201, 372 (1971).
V. A. Budylin, M. S. Ermolenko, F. A. Chugmai, and A. N. Kost, Khim. Geterotsikl. Soedin., 1494 (1981).
R. Hoffman, J. M. Howell, and E. L. Muetterties, J. Am. Chem. Soc.,94, 3047 (1972).
V. I. Bregadze, V. Ts. Kampel, and N. N. Godovnikov, J. Organomet. Chem.,112, 249 (1976).
H. Meerwein, Org. Synth.,46, 113 (1966).
V. I. Stanko, V. A. Brattsev, N. N. Ovsyannikov, and T. P. Klimova, Zh. Obshch. Khim.,44, 2482 (1974).
L. I. Zakharkin and V. N. Kalinin, Dokl. Akad. Nauk SSSR,169, 590 (1966).
I. G. Ryss and S. L. Idel's, Zh. Neorg. Khim.,2, 2270 (1957).
A. N. Nesmeyanov and L. G. Makarova, Izv. Akad. Nauk SSSR, Otdel. Khim. Nauk, 617 (1945).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2111–2116, September, 1985.
Rights and permissions
About this article
Cite this article
Grushin, V.V., Demkina, I.I. & Tolstaya, T.P. Reactions of bromonium salts of the carboborane series with nucleophiles. Russ Chem Bull 34, 1950–1955 (1985). https://doi.org/10.1007/BF00953942
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00953942