Skip to main content
SpringerLink
Log in

1,2-Adducts of 5-Allyl-2,3,5-trichloro-4,4-dimethoxy-2-cyclopentenone with Ethyl Acetate Lithium Salt and Their Reactions with Iodine

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

The condensation of 5-allyl-2,3,5-trichloro-4,4-dimethoxy-2-cyclopentenone with ethyl acetate lithium salt generated in situ in THF at -78°C gave adducts at the carbonyl group, the corresponding cis- and trans-chlorohydrins. The steric structure of the products was determined by involving them into reaction with iodine. From the trans-adduct the expected bicyclic compound was obtained, while the cis-chlorohydrin underwent anomalous deacetalization to iodomethoxycyclopentenone. Spectral parameters of the adducts were discussed. Unusual diastereotopicity was observed for the remote methylene groups in the ester moiety.

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

REFERENCES

  1. Akhmetvaleev, R.R., Imaeva, L.R., Belogaeva, T.A., and Miftakhov, M.S., Russ. J. Org. Chem., 1999, vol. 35, no. 2, pp. 238-241.

    Google Scholar 

  2. Shomo, L., Ishifine, M., and Kashimura, S., Chem. Lett., 1990, no. 3, pp. 449-452.

  3. Cardillo, G. and Orena, M., Tetrahedron, 1990, vol. 46, no. 10, pp. 3321-3408.

    Google Scholar 

  4. Akbutina, F.A., Torosyan, S.A., Vostrikov, N.S., Spirikhin, L.V., and Miftakhov, M.S., Izv. Ross. Akad. Nauk, Ser. Khim., 1996, no. 12, pp. 2961-2963.

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Bashkortostan, Russia

    N. S. Vostrikov, V. Z. Vasikov, L. V. Spirikhin & M. S. Miftakhov

Authors
  1. N. S. Vostrikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. Z. Vasikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. L. V. Spirikhin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. S. Miftakhov
    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

Vostrikov, N.S., Vasikov, V.Z., Spirikhin, L.V. et al. 1,2-Adducts of 5-Allyl-2,3,5-trichloro-4,4-dimethoxy-2-cyclopentenone with Ethyl Acetate Lithium Salt and Their Reactions with Iodine. Russian Journal of Organic Chemistry 38, 651–654 (2002). https://doi.org/10.1023/A:1019698603236

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1019698603236

Keywords

Search

Navigation