Summary
-
1.
In the oxidation of 1,5-diphenyl-3-pentadienone (IV) and of 1-cyclohexen-1-yl propenyl ketone (VI) with alkaline hydrogen peroxide, in each case two geometric isomers of the corresponding α-keto diepoxide were isolated.
-
2.
It is suggested that the hydrogen peroxide oxidation reaction is accompanied by inversion of the configuration of the original α, β - unsaturated ketone.
Similar content being viewed by others
Literature cited
I. N. Nazarov and A. A. Arkhem, Bull. Acad. Sci. USSR, Div. Chem. Sci. 1950, 621.
E. Weitz, A. Scheffer, Ber. 54, 2327 (1921).
S. Bodfors, Ber. 49, 2795 (1916).
R. Lutz, R. Jordan, J. Am. Chem. Soc. 72, 4090 (1950); R. Lutz et al., J. Am. Chem. Soc. 75, 5990 (1953); 72, 4300 (1950).
H. Wasserman et al., J. Am. Chem. Soc. 75, 96 (1953); 77, 590 (1955).
N. Cromwell, R. Setterquist, J. Am. Chem. Soc. 76, 2752 (1954).
S. Bodfors, Ber. 51, 192 (1918).
Organic Syntheses, Vol. 2, Moscow, 1950, p. 179.
C. Bunton, G. Minkoff, J. Chem. Soc. 1949, 665.
I. N. Nazarov and L. N. Pinkina, Bull. Acad. Sci. USSR, Div. Chem. Sci. 1946, 633; I. N. Nazarov, A. A. Arkhem, and I. G. Tishchenko, J. Gen. Chem. 25, 708 (1955).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Nazarov, I.N., Arkhem, A.A. α-keto epoxides and their reactions Communication 7. Geometric isomerism in theα-keto diepoxide series. Russ Chem Bull 5, 1499–1503 (1956). https://doi.org/10.1007/BF01177531
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF01177531