Kinetic Stabilization of <i>N</i>,<i>N</i>‑Dimethyl-2-propyn-1-amine <i>N</i>‑Oxide by Encapsulation

Thermally and in nonprotic media <i>N</i>,<i>N</i>-dimethyl-2-propyn-1-amine <i>N</i>-oxide undergoes two consecutive sigmatropic rearrangements affording propenal. Two molecular containers capable of the quantitative inclusion/encapsulation of the <i>N</i>-oxide are described. The <i>N</i>-oxide becomes kinetically stabilized when included in the containers. The relationship between the observed kinetic stabilization of the <i>N</i>-oxide and the thermodynamic and kinetic stability of its inclusion complexes is explained and modeled.