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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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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.

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Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Armenia, ul. Z. Kanakertsi 167a, Erevan, 375091, Armenia

    E. O. Chukhadzhyan, A. R. Gevorkyan & M. K. Nalbandyan

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  1. E. O. Chukhadzhyan
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  2. A. R. Gevorkyan
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  3. M. K. Nalbandyan
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Original Russian Text © E.O. Chukhadzhyan, A.R. Gevorkyan, M.K. Nalbandyan, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 12, pp. 1784–1787.

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Chukhadzhyan, E.O., Gevorkyan, A.R. & Nalbandyan, M.K. 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. Russ J Org Chem 42, 1771–1774 (2006). https://doi.org/10.1134/S1070428006120025

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  • DOI: https://doi.org/10.1134/S1070428006120025

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