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Synthesis of 3E-tetradecenol, 3E, 9E-tetradecadienol, and their acetates starting from acetylcyclopropane

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Abstract

Stereospecific synthesis of the linear E-olefins mentioned in the title was realized by a general scheme that was worked out earlier by the authors and which includes as key steps homologization of the corresponding aliphatic pentakisnoraldehydes by means of trimethylsilyloxyvinylcyclopropane and ZnBr2-initiated rearrangement of the intermediate cyclopropylcarbinols under the influence of Me3SiBr.

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Authors and Affiliations

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

    N. M. Ivanova, B. A. Cheskis, E. V. Rubanova, V. G. Yatsynin, A. M. Moiseenkov & O. M. Nefedov

  2. Scientific and Industrial Association “Kuban'zerno,”, Krasnodar

    N. M. Ivanova, B. A. Cheskis, E. V. Rubanova, V. G. Yatsynin, A. M. Moiseenkov & O. M. Nefedov

Authors
  1. N. M. Ivanova
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  2. B. A. Cheskis
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  3. E. V. Rubanova
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  4. V. G. Yatsynin
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  5. A. M. Moiseenkov
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  6. O. M. Nefedov
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 640–644, March, 1991.

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Ivanova, N.M., Cheskis, B.A., Rubanova, E.V. et al. Synthesis of 3E-tetradecenol, 3E, 9E-tetradecadienol, and their acetates starting from acetylcyclopropane. Russ Chem Bull 40, 557–561 (1991). https://doi.org/10.1007/BF00957995

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  • DOI: https://doi.org/10.1007/BF00957995

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