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


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.


EtOH Allyl Piperidine Morpholine Ammonium Bromide 
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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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