Mechanical Force Induces Ylide-Free Cycloaddition of Nonscissible Aziridines

Sangmin Jung

Reported herein is that aziridines can be a nonvulnerable mechanophore. Upon exposure to a mechanical force, stereochemically pure nonactivated aziridines incorporated into the backbone of macromolecule do not undergo cis‐trans isomerization, evidencing no bond cleavage by the force. Nonetheless, aziridines react with a dipolarophile and does not obey conventional reaction pathways that involve C‐C or C‐N bond cleavage prior to the event of cycloaddition. The mechanism of such an ylide‐free reaction of aziridines is explained by calculations. Our work demonstrates that a nonvulnerable chemical structure can be a mechanophore.

https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201915438