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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

1992; Royal Society of Chemistry; Issue: 2 Linguagem: Inglês

10.1039/c39920000132

2050-5639

Michèle Dessolin, Odile Eisenstein, M. GOLFIER, T. Prangé, Philippe Sautet,

Chemical Reactions and Mechanisms

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.