Conclusions
-
1.
Platinum metal compounds and cupric chloride catalyze the splitting of the C-C bonds in β-diketones with the formation of ketones and esters, and in acetoacetic ester with the formation of acetone. Trifluoroacetylacetone is split with more difficulty than acetylacetone, while hexafluoroacetylacetone does not split at the C-C bond under the conditions studied.
-
2.
The activity series of the MCl2 salts in splitting acetylacetone in an alcoholic solution coincides with the series of the complexing ability.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature cited
S. Livingstone, Chemistry of Ruthenium, Rhodium, Palladium, Osmium, Iridium, and Platinum [Russian translation], Mir, Moscow (1978).
I. S. Akhrem, R. S. Vartanyan, L. E. Kotlyar, and M. E. Vol'pin, Izv. Akad. Nauk SSSR, Ser. Khim., 253 (1977).
K. Kaneda, H. Azuma, M. Wayaku, and S. Teranishi, Chem. Lett.,3, 215 (1974).
R. G. Pearson and A. G. Sandy, J. Am. Chem. Soc.,73, 931 (1951).
J. E. Meany, J. Phys. Chem.,73, 3421 (1963).
C. M. Harris and S. E. Livingstone, Chelating Agents and Metallic Chelates, Academic Press, N.Y. (1964), p. 95.
B. G. Shultz and E. M. Larsen, J. Am. Chem. Soc,71, 3250 (1949).
K. Sato, J. Kodama, and K. Arakawa, J. Chem. Soc. Jpn., Pure Chem. Sect.,87, 821 (1966).
K. Sato and O. Kammori, Bull. Chem. Soc. Jpn.,42, 2778 (1969).
K. I. Pashkevich, V. I. Saloutin, and I. Ya. Postovskii, Usp. Khim.,2, 329 (1981).
R. F. Heck, J. Am. Chem. Soc.,90, 5518 (1968).
F. P. Dwyer and A. M. Sargeson, J. Am. Chem. Soc.,75, 984 (1953).
J. A. Osborn, F. H. Jardine, I. F. Young, and G. Wilkinson, J. Chem. Soc., A, No. 12, 1711 (1966).
W. B. Renfrow and A. Renfrow, J. Am. Chem. Soc.,68, 1801 (1946).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1346–1350, June, 1983.
The authors wish to express their gratitude to E. I. Mysov for taking the mass spectra.
Rights and permissions
About this article
Cite this article
Akhrem, I.S., Vartanyan, R.S., Afanas'eva, L.V. et al. Splitting of C-C bonds in β-dicarbonyl compounds catalyzed by transition metal complexes. Russ Chem Bull 32, 1217–1220 (1983). https://doi.org/10.1007/BF00953160
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00953160