Conclusions
-
1.
Rhodium complexes [(RhCl (COD)]2, RhCl(PPh3)3, and RhCl3 immobilized on silica gel modified by amino and aminophosphine groups catalyze selective reduction of nitrobenzene into aniline in Ar medium (25–82.4°C) by transfer of hydrogen from 2-propanol (KOH promotor) and sodium borohydride.
-
2.
The rate of reduction of nitrobenzene by sodium borohydride is one to two orders of magnitude higher than with 2-propanol.
-
3.
Incorporation of a halogen in the benzene ring results in a decrease in the rate of reduction of the nitro group. Reduction of halonitrobenzenes by sodium borohydride takes place in two stages: The NO2 group is reduced first, and the halogen is then cleaved.
Similar content being viewed by others
Literature cited
V. F. Dovganyuk, V. I. Isaeva, and V. Z. Sharf, Izv. Akad. Nauk SSSR, Ser. Khim., No. 6, 1223 (1988).
V. Z. Sharf, L. Kh. Freidlin, B. M. Savchenko, and V. N. Krutii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 5, 1134 (1979).
K. Hanaya, T. Muramatsu, H. Kudo, and Y. L. Show, J. Chem. Soc. Perkin Trans. 1, No. 40, 2409 (1979).
V. F. Dovganyuk, A. I. Lafer, V. I. Isaeva, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2660 (1987).
C. W. Parshal, Acc. Chem. Res.,3, No. 4, 139 (1970).
S. Z. Bernadyuk, G. V. Kudryavtsev, and G. V. Lisichkin, Koord. Khim.,5, No. 12, 1834 (1979).
B. Viswanathan and D. Ramesh, Polyhedron, No. 6, 345 (1987).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 534–539, March 1989.
Rights and permissions
About this article
Cite this article
Sharf, V.Z., Dovganyuk, V.F., Isaeva, V.I. et al. Study of the catalytic activity of metal complexes attached to a solid support. 6. Reduction of nitrobenzene and its halogenated derivatives by chemically bound hydrogen in the presence of immobilized Rh complexes. Russ Chem Bull 38, 468–472 (1989). https://doi.org/10.1007/BF00958034
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00958034