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Stereochemistry of the wittig reaction withβ-ionone

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

Summary

  1. 1.

    Independent of the solvent and the proton acceptor, a mixture of the cis-trans isomers of ethyl α-ionylideneacetate is formed when (C2H5)2P(O)CH2OOC2H5 is reacted with α-ionone.

  2. 2.

    Independent of the proton acceptor (NaNH2 or NaH), the trans-isomer of ethyl β-ionylideneacetate is formed predominantly when (C2H5)2P(O)CH2COOC2K5 is reacted with β-ionone in tetrahydrofuran medium, while a mixture of the cis-trans isomers is obtained in dimethylformamide medium (proton acceptor -C2H5ONa, NaH or NaNH2).

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Literature cited

  1. J. Isikawa, Bull. Chem. Soc. Japan36, 1527 (1963); J. Chem. Soc. Japan (Pure Chem. Sec.)84, 991 (1963).

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  2. B. G. Kovalev, L. A. Yanovskaya, and V. F. Kucherov, Izv. AN SSSR, Otd. Khim. Nauk, 857 (1963).

  3. L. A. Yanovskaya, and V. F. Kucherov, Izv. AN SSSR, Ser. Khim. 1341 (1964).

  4. Zh. A. Krasnaya and V. F. Kucherov, Izv. AN SSSR, Otd. Khim. Nauk, 1057 (1962).

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, USSR

    L. A. Yanovskaya & V. F. Kucherov

Authors
  1. L. A. Yanovskaya
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  2. V. F. Kucherov
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Additional information

Translated from Izvestiya Akadeemii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1504–1506, August, 1965 Original article submitted December 18, 1964

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Yanovskaya, L.A., Kucherov, V.F. Stereochemistry of the wittig reaction withβ-ionone. Russ Chem Bull 14, 1475–1477 (1965). https://doi.org/10.1007/BF00846222

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  • DOI: https://doi.org/10.1007/BF00846222

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