Mechanical Force Induces Ylide-Free Cycloaddition of Nonscissible Aziridines.

Mechanical Force Induces Ylide-Free Cycloaddition of Nonscissible Aziridines.
Angew Chem Int Ed Engl. 2020 Jan 16;:
Authors: Yoon HJ, Jung S
Abstract
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.
PMID: 31944507 [PubMed - as supplied by publisher]

Source: Angewandte Chemie - January 15, 2020 Category: Chemistry Authors: Yoon HJ, Jung S Tags: Angew Chem Int Ed Engl Source Type: research