Thermally and in nonprotic media N,N-dimethyl-2-propyn-1-amine N-oxide undergoes two consecutive sigmatropic rearrangements affording propenal. Two molecular containers capable of the quantitative inclusion/encapsulation of the N-oxide are described. The N-oxide becomes kinetically stabilized when included in the containers. The relationship between the observed kinetic stabilization of the N-oxide and the thermodynamic and kinetic stability of its inclusion complexes is explained and modeled.
Kinetic Stabilization of N,N-Dimethyl-2-propyn-1-amine N-Oxide by Encapsulation
Org. Lett. 2013, 15, 4976-4979.