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

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.