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Chemistry of cyclopentenones communication 6. Transformations of erythro and threo isomers of 5-(1-acetoxyethyl)-3,5-dimethylcyclopenten-1-ones

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Summary

  1. 1.

    It was established that erythro-threo isomerism occurs in the products isolated in the condensation of 3,5-dimethyl-2-cyclopenten-1-one with vinyl acetate.

  2. 2.

    On the basis of chemical and spectroscopic data it was shown that 5-(1-acetoxyethyl)-3,5-dimethyl-2-cyclopenten-1-one (IA) (m.p. 69–70°) is the more stable isomer and it was assigned the erythro configuration; its epimer (IB) was assigned the threo configuration.

  3. 3.

    It was shown that isomerization at the asymmetric center at C-6 leads to the conversion of compounds of the “B” series into “A” compounds in the course of the formation of the 2,4-dinitrophenylhydrazones of (IB) and(VIB) and in the hydrogenation of the (1-acetoxyethyl)cyclopentenones (IIIB) and IVB) over a platinum catalyst. A suggestion is made concerning the mechanism of these isomerizations.

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Literature cited

  1. 1.

    A. N. Elizarova, T. E. Pozdnyakova, and A. A. Akhrem, izv. AN SSSR, Otd. khim. n.1962, 2167.

  2. 2.

    N. M. Cullinane and B. F. R. Edwards, J. Chem. Soc.1958, 1311.

  3. 3.

    B. Ellis (Mrs.), S. P. Hall, V. Petrow (Mrs), and S. Waddington, Feater, J. Chem. Soc.1961, 4111.

  4. 4.

    V. G. Brystrov, T. E. Pozdynakova, A. N. Elizarova, and A. A. Akhrem, Izv. AN SSSR, Otd. khim. n.1963, 66.

  5. 5.

    I. N. Nazarov, I. I. Zaretskaya, Izv. AN SSSR, Otd. khim. n.1944, 65.

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Additional information

This paper is published in accordance with a resolution of the Conference of Chief Editors of Journals of the Academy of Sciences of the USSR of July 2, 1962, as a dissertation paper by T. E. Pozdnyakova.

The authors take this opportunity of expressing their thanks to B. V. Lopatin and T. M. Fadeeva for the determination of infrared and ultraviolet spectra.

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Elizarova, A.N., Pozdnyakova, T.E. & Akhrem, A.A. Chemistry of cyclopentenones communication 6. Transformations of erythro and threo isomers of 5-(1-acetoxyethyl)-3,5-dimethylcyclopenten-1-ones. Russ Chem Bull 12, 113–119 (1963). https://doi.org/10.1007/BF00846960

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Keywords

  • Hydrogenation
  • Acetate
  • Platinum
  • Vinyl
  • Spectroscopic Data