A Retro-Staudinger Cycloaddition: Mechanochemical Cycloelimination of a β-Lactam Mechanophore

Maxwell J. Robb, Jeffrey S. Moore

Research output: Contribution to journalArticlepeer-review

Abstract

Mechanical activation of a β-lactam mechanophore using ultrasound induces a formal [2 + 2] cycloelimination reaction producing ketene and imine functional groups - the reverse reaction of the Staudinger cycloaddition. This transformation is predicted by computational modeling and verified by kinetics and UV-vis absorption measurements as well as polymer end-group analysis using 1H and 13C NMR spectroscopy. Addition of the β-lactam motif to the current repertoire of covalent mechanophores coupled with the diverse reactivity of the ketene functional group provides a promising new platform for achieving materials capable of autonomic self-healing behavior in response to external forces.

Original languageEnglish (US)
Pages (from-to)10946-10949
Number of pages4
JournalJournal of the American Chemical Society
Volume137
Issue number34
DOIs
StatePublished - Sep 2 2015

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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