Die Umlagerung substituierter Aminoacrylderivate

Abstract

The addition of proton acids as HF, HCl, HBr and HOAc to acetylenes of the type (CH₃)₂N–C=C–CO–R (1) yields, after rearrangement of the very instable primary adducts (2), the β-substituted acrylamides (3). The rate of the rearrangement depends both on the nature of the halogen and the carbonyl substituent R: It increases in the series F < Cl < Br ≅ OAc and decreases in the series R=H ≧ CH₃ ≫ OCH₃. The rearrangement is catalysed by traces of acid.