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Stereochemistry of cyclic compounds

Communication 50. Oxidation of cis-syn-3a,4,5,6-tetrahydro-4,5-indandicarboxylic anhydride

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

Summary

  1. 1.

    The oxidation of the cis-syn anhydride (II) with peroxyacetic acid proceeds stereospecifically and leads to the formation of the epoxy anhydride (III) with a cis disposition of the anhydride and epoxy rings.

  2. 2.

    The opening of the epoxy ring in the epoxy anhydride (III) under the action of hydrogen chloride and of water was studied. On the basis of certain reactions and the infrared spectra conclusions were reached concerning the structures of the products then formed.

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Literature cited

  1. V. F. Kucherov, É. P. Serebryakov, and A. V. Usova, Izv. AN SSSR. Otd. khim. n. 1962 (in the press).

  2. V. F. Kucherov, G. M. Segal', I. N. Nazarov, Izv. AN SSSR. Otd. khim. n. 1959, 1253.

  3. V. F. Kucherov and É. P. Serebryakov, Izv. AN SSSR. Otd. khim. n. 1961, 1087.

  4. V. F. Kucherov, I. V. Berezin and I. N. Nazarov, Izv. AN SSSR. Otd. khim. n. 1958,186.

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Kucherov, V.F., Serebryakov, E.P. Stereochemistry of cyclic compounds. Russ Chem Bull 11, 611–615 (1962). https://doi.org/10.1007/BF00904762

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  • DOI: https://doi.org/10.1007/BF00904762

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