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
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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.
KeywordsEtOH Allyl Piperidine Morpholine Ammonium Bromide
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- 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.Babayan, A.T., Ananyan, E.S., and Chukhadzhyan, E.O., Arm. Khim. Zh., 1969, vol. 22, p. 894.Google Scholar
- 3.Chukhadzhyan, El.O., Chukhadzhyan, E.O., and Babayan, A.T., Zh. Org. Khim., 1974, vol. 10, p. 46.Google Scholar
- 4.Babayan, A.T., Tagmazyan, K.Ts., and Ananyan, E.S., Zh. Org. Khim., 1966, vol. 2, p. 1984.Google Scholar
- 5.Ananyan, E.S., Tagmazyan, K.Ts., and Babayan, A.T., Arm. Khim. Zh., 1969, vol. 22, p. 894.Google Scholar
- 6.Mannich, C., Chem. Ber., 1933, vol. 66, p. 418.Google Scholar
- 7.Chukhadzhyan, E.O., Gabrielyan, G.L., and Babayan, A.T., Arm. Khim. Zh., 1976, vol. 29, p. 452.Google Scholar
- 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.Chukhadzhyan, E.O., Gevorkyan, A.R., Chukhadzhyan, El.O., and Shakhatuni, K.G., Russ. J. Org. Chem., 2000, vol. 36, p. 1263.Google Scholar