Skip to main content
SpringerLink
Log in

Stereochemistry of heterocyclic compounds

Communication 2. Geometric isomers of 1-cyclohexyl-and 1-phenyl-2.5-dimethyl-4-phenylpiperidols-4

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

Summary

  1. 1

    Isomerization of 1-cyclohexyl-trans-2,5-dimethylpiperidone with Al2O3 yielded 1-cyclohexyl-cis-2,5-dimethylpiperidone-4, which reacted with phenyllithium to give one isomer of 1-cyclohexyl-2,5-dimethyl-4-phenylpiperidol-4. On the basis of a series of chemical conversions, this isomer was assigned the configuration (V), which contains the methyl and phenyl groups in the cis-position.

  2. 2.

    Isomerization of the latter yielded a new isomer of this alcohol, which was apparently its epimer at C4.

  3. 3.

    By analogous conversions of 1-phenyl-trans-2,5-dimethylpiperidone-4 it was possible to obtain the isomeric 1-phenyl-2,5-dimethyl-4-phenylpiperidol-4, which apparently had the methyl groups in the cis-position.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature cited

  1. I. N. Nazarov, et al.. Zh. obshch. khimii25, 2245 (1955).

    Google Scholar 

  2. I. N. Nazarov, S. G. Matsoyan, and V. A. Rudenko, Izvest. Akad. Nauk SSSR, Otdel. Khim. Nauk1952, 1057.

  3. I. N. Nazarov, N. I. Shvetsov, and O. I. Sorokin, Zhur. Obshchei Khim.26, 3157 (1956).

    Google Scholar 

  4. I. N. Nazarov, S. G. Matsoyan, and V. A. Rudenko, Izvest. Akad. Nauk SSSR, Otdel. Khim. Nauk1953. 303.

  5. N. I. Shvetsov and V. F. Kucherov, Doklady Akad. Nauk SSSR126, 1017 (1955).

    Google Scholar 

  6. I. N. Nazarov and N. I. Shvetsov, Izvest. Akad. Nauk SSSR, Otdel. Khim. Nauk1959 2161.

Download references

Author information

Authors and Affiliations

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

    V. F. Kucherov & N. I. Shvetsov

Authors
  1. V. F. Kucherov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. I. Shvetsov
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kucherov, V.F., Shvetsov, N.I. Stereochemistry of heterocyclic compounds. Russ Chem Bull 10, 263–267 (1961). https://doi.org/10.1007/BF00919563

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00919563

Keywords

Search

Navigation