Summary
Cases of the different chemical behavior of aliphatic and cyclic β-dicarbonyl compounds have been considered. The following properties are characteristic for β -diketones of the type of dihydroresorcinol: hindered Michael and C-alkylation reactions, tendency to form alkylidene-bis-β-diketones by the action of aldehydes, incapability of undergoing the Mannich reaction, inertness of the halogen atom of enolized 2-bromo derivatives, and the brominatioh of the enol ethers by N-bromosuccinimide in the second position.
Similar content being viewed by others
Literature cited
G. Schwarzenbach, E. Felder, Helv. chim. acta27, 1044 (1944).
S. I. Zav'yalov. Collection of Papers at the Conference on the Structure and Reactivity of Organic Compounds in Leningrad [in Russian] Goskhimizdat, 1959, p. 24.
M. I. Kabachnik. Dokl. AN SSSR,83, 859 (1952).
C. S. Misra, J. S. Shukla, J. Indian Chem. Soc.29, 455 (1952).
I. N. Nazarov, S. I. Zav'yalov, and M. S. Burmistrova, Izv. AN SSSR. Otd. khim. n., 205 (1956).
I. I. Nazarov and S. I. Zav'yalov, Izv. AN SSSR, Otd. khim. n. 325 (1957).
H. Stetter, W. Dierichs, Chem. Ber.85, 61 (1952).
F. E. King, D. G. Felton, J. Chem. Soc. 1371 (1948).
D. Vorlander, Liebigs Ann. Chem.294, 316 (1897).
H. Hellman, G. Opitz, Liebigs Ann. Chem.604, 214 (1957).
S. I. Zav'yalov, VIIIth Mendeleev Conference, Section of Organic Chemistry and Technology [in Russian], Izd. AN SSSR, 1959, p. 223.
M. Conrad, C. Buckner, Ber.24, 2998 (1891).
I. N. Nazarov and S. I. Zav'yalov. Izv. AN SSSR, Otd. khim. n. 200 (1958).
D. Kostermans, Recueil. trav. chim.70, 79 (1951).
I. N. Nazarov and S. I. Zav'yalov, Izv. AN SSSR, Otd. khim. n. 668 (1959).
K. Arakawa, Pharm. Bull. Japan5, 528 (1957).
B. Eistert et al., Chem. Ber.84, 1956 (1951).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Zav'yalov, S.I., Vinogradova, L.P. β-Dicarbonyl compounds. Russ Chem Bull 10, 1529–1533 (1961). https://doi.org/10.1007/BF00906146
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00906146