Mechanical Force Induces Ylide-Free Cycloaddition of Nonscissible Aziridines

Sangmin Jung, Hyo Jae Yoon

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The application of aziridines as nonvulnerable mechanophores is reported. Upon exposure to a mechanical force, stereochemically pure nonactivated aziridines incorporated into the backbone of a macromolecule do not undergo cis–trans isomerization, thus suggesting retention of the ring structure under force. Nonetheless, aziridines react with a dipolarophile and seem not to obey conventional reaction pathways that involve C−C or C−N bond cleavage prior to the cycloaddition. Our work demonstrates that a nonvulnerable chemical structure can be a mechanophore.

Original languageEnglish
JournalAngewandte Chemie - International Edition
DOIs
Publication statusAccepted/In press - 2020 Jan 1

Keywords

  • aziridines
  • cycloaddition
  • mechanochemistry
  • mechanophores
  • stereoselectivity

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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