A double ionic mechanism for the Chapman-like rearrangement of imino-ethers to N-alkylmides, in the solid state or in the melt. Theoretical and experimental evidence

Abstract

Using 5-methoxy-2-aryl-1,3,4-oxadiazoles as models it was shown that the thermal rearrangement of imino-ethers to N-alkylamides proceeds through a double ionic mechanism; kinetic measurements in the solid state and in the melt give apparent activation energies that support ab initio calculated activation enthalpies.