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Russian Journal of Organic Chemistry

, Volume 42, Issue 12, pp 1771–1774 | Cite as

Synthesis of dialkyl(1-allyl-3-arylprop-2-yn-1-yl)-and dialkyl(1-allyl-3-alkenylprop-2-yn-1-yl)amines by the stevens rearrangement

  • E. O. Chukhadzhyan
  • A. R. Gevorkyan
  • M. K. Nalbandyan
Article

Abstract

The Stevens rearrangement of dialkyl(allyl)(3-arylprop-2-yn-1-yl)-and dialkyl(allyl)(3-alkenyl-prop-2-yn-1-yl)ammonium bromides gave dialkyl(1-allyl-3-arylprop-2-yn-1-yl)-and dialkyl(1-allyl-3-alkenyl-prop-2-yn-1-yl)amines. Here, the allyl group acts as migrating group, and 3-aryl-or 3-alkenylprop-2-yn-1-yl, as receiving one. The yields of the Stevens rearrangement products fall down as the alkyl chain becomes longer, as well as with introduction of a methyl group into the meta or para position of the aromatic ring.

Keywords

EtOH Allyl Piperidine Morpholine Ammonium Bromide 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    Chukhadzhyan, E.O., Chukhadzhyan, El.O., Shakhatuni, K.G., Manasyan, L.A., and Babayan, A.T., Khim. Geterotsikl. Soedin., 1994, no. 2, p. 213.Google Scholar
  2. 2.
    Babayan, A.T., Ananyan, E.S., and Chukhadzhyan, E.O., Arm. Khim. Zh., 1969, vol. 22, p. 894.Google Scholar
  3. 3.
    Chukhadzhyan, El.O., Chukhadzhyan, E.O., and Babayan, A.T., Zh. Org. Khim., 1974, vol. 10, p. 46.Google Scholar
  4. 4.
    Babayan, A.T., Tagmazyan, K.Ts., and Ananyan, E.S., Zh. Org. Khim., 1966, vol. 2, p. 1984.Google Scholar
  5. 5.
    Ananyan, E.S., Tagmazyan, K.Ts., and Babayan, A.T., Arm. Khim. Zh., 1969, vol. 22, p. 894.Google Scholar
  6. 6.
    Mannich, C., Chem. Ber., 1933, vol. 66, p. 418.Google Scholar
  7. 7.
    Chukhadzhyan, E.O., Gabrielyan, G.L., and Babayan, A.T., Arm. Khim. Zh., 1976, vol. 29, p. 452.Google Scholar
  8. 8.
    Gevorkyan, A.R., Chukhadzhyan, E.O., Chukhadzhyan, El.O., and Panosyan, G.A., Khim. Geterotsikl. Soedin., 2004, no. 2, p. 212.Google Scholar
  9. 9.
    Chukhadzhyan, E.O., Gevorkyan, A.R., Chukhadzhyan, El.O., and Shakhatuni, K.G., Russ. J. Org. Chem., 2000, vol. 36, p. 1263.Google Scholar

Copyright information

© Pleiades Publishing, Inc. 2006

Authors and Affiliations

  • E. O. Chukhadzhyan
    • 1
  • A. R. Gevorkyan
    • 1
  • M. K. Nalbandyan
    • 1
  1. 1.Institute of Organic ChemistryNational Academy of Sciences of ArmeniaErevanArmenia

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