Mechanical Force for the Transformation of Aziridine into Imine

Force-selective mechanochemical reactions may be important for applications in polymer mechanochemistry, yet it is difficult to achieve such reactions. This paper reports that cis-N-phthalimidoaziridine incorporated into a macromolecular backbone undergoes migration of N-phthalimido group to afford imine under mechanochemical condition and not thermal one. The imine is further hydrolyzed by water bifurcating into amine and aldehyde. These structural transformations are confirmed by H-1 NMR and FT-IR spectroscopic analyses. Computational simulations are conducted for the aziridine mechanophore to propose the mechanism of reaction and define the substrate scope of reaction.

Automated summary

This study reports the incorporation of cis-N-phthalimidoaziridine into a macromolecular backbone, leading to the migration of the N-phthalimido group to form an imine under mechanochemical conditions. The imine is then hydrolyzed by water to produce amine and aldehyde. Structural transformations are confirmed through H-1 NMR and FT-IR spectroscopic analyses, and computational simulations are used to propose the reaction mechanism and define the substrate scope.