Skip to main content
SpringerLink
Log in

Acid hydrolysis of amides obtained by Beckmann rearrangement of methyl ketones oximes of unsaturated γ-lactone, aromatic, and alicyclic series

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

Abstract

Beckmann rearrangement was performed of oximes of substituted 3-acetyl-4-methyl-5,5-dimethyl(pentamethylene)-2-oxo-2,5-dihydrofuranes in the presence of boron trifluoride etherate. Aiming at establishing the spatial arrangement of the oximes the hydrolysis was carried out of acid amides obtained by Beckmann rearrangement of oximes of methyl ketones belonging to unsaturated γ-lactone series and also to aromatic and alicyclic series. The hydrolysis with 20% sulfuric acid led to the formation of the corresponding acid and amine, and the hydrolysis with acetic and hydrochloric acids resulted in retrobeckmann rearrangement giving the initial oximes.

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. Beckmann, E. Ber. 1886, vol. 19, p. 988.

    Google Scholar 

  2. Avetisyan, A.A., Tokmadzhyan, G.G., Margaryan, A.X., Ovsepyan, V.V., and Bakhshinyan, R.V., Khim. Geterotsikl. Soedin., 1989, p. 157.

  3. Knunyants, I.L. and Fabrichnyi, B.P., Usp. Khim., 1949, vol. 18, p. 633.

    CAS  Google Scholar 

  4. Shriner, R. L., Fuson, R. C., Curtin, D. Y., and Morrill, T.C., The Systematic Identification of Organic Compounds. A Laboratory Manual, New York: Wiley 1978.

    Google Scholar 

  5. Avetisyan, A.A., Tatevosyan, G.E., and Dangyan, M.T., Arm. Khim. Zh., 1971, vol. 24, p. 688.

    Google Scholar 

  6. Avetisyan, A.A., Tatevosyan, G.E., and Dangyan, M.T., Arm. Khim. Zh., 1971, vol. 24, p. 777.

    CAS  Google Scholar 

  7. Kyziok, J.B. and Lyzniak, A., Tetrahedron, 1980, vol. 36, p. 3017.

    Article  Google Scholar 

  8. Slovar’ Org. Soed. (Dictionary of Organic Compounds), 1949, vol. 1, p. 15.

  9. Beckmann, E., Lieb. Ann., 1909, vol. 365, p. 208.

    Article  Google Scholar 

  10. Sint. Org. Soed. (Synthesis of Organic Compounds), 1949, vol. 1, p. 224.

  11. Metody polucheniya khimicheskikh reaktivov i preparatov (Technics of Synthesis of Chemicals Reagents), Moscow: IREA, 1961, p. 12.

  12. Temnikova, T.I., Kurs teoreticheskix osnov organicheskoi khimii (Course of Theoretical Princicples of Organic Chemistry), Leningrad: Khimiya, 1968, p. 622.

    Google Scholar 

  13. Temnikova, T.I., Kurs teoreticheskix osnov organicheskoi khimii (Course of Theoretical Princicples of Organic Chemistry), Leningrad: Khimiya, 1968, p. 596.

    Google Scholar 

  14. Langhals, H. and Ruchardt, Ch., Ber., 1981, vol. 114, p. 3881.

    Google Scholar 

  15. Sint. Org. Soed. (Synthesis of Organic Compounds), 1949, vol. 1, p. 269.

Download references

Author information

Authors and Affiliations

  1. Erevan State University, Erevan, 375025, Armenia

    G. G. Tokmadzhyan

Authors
  1. G. G. Tokmadzhyan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to G. G. Tokmadzhyan.

Additional information

Original Russian Text © G.G. Tokmadzhyan, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 11, pp. 1708–1711.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Tokmadzhyan, G.G. Acid hydrolysis of amides obtained by Beckmann rearrangement of methyl ketones oximes of unsaturated γ-lactone, aromatic, and alicyclic series. Russ J Org Chem 47, 1746–1749 (2011). https://doi.org/10.1134/S1070428011110170

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428011110170

Keywords

Search

Navigation