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α-keto epoxides and their reactions Communication 7. Geometric isomerism in theα-keto diepoxide series

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 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. 2.

    It is suggested that the hydrogen peroxide oxidation reaction is accompanied by inversion of the configuration of the original α, β - unsaturated ketone.

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Literature cited

  1. I. N. Nazarov and A. A. Arkhem, Bull. Acad. Sci. USSR, Div. Chem. Sci. 1950, 621.

  2. E. Weitz, A. Scheffer, Ber. 54, 2327 (1921).

    Google Scholar 

  3. S. Bodfors, Ber. 49, 2795 (1916).

    Google Scholar 

  4. 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).

    Google Scholar 

  5. H. Wasserman et al., J. Am. Chem. Soc. 75, 96 (1953); 77, 590 (1955).

    Google Scholar 

  6. N. Cromwell, R. Setterquist, J. Am. Chem. Soc. 76, 2752 (1954).

    Google Scholar 

  7. S. Bodfors, Ber. 51, 192 (1918).

    Google Scholar 

  8. Organic Syntheses, Vol. 2, Moscow, 1950, p. 179.

  9. C. Bunton, G. Minkoff, J. Chem. Soc. 1949, 665.

  10. 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).

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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

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  • DOI: https://doi.org/10.1007/BF01177531

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