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

Robb, Maxwell J. and Moore, Jeffrey S. (2015) A Retro-Staudinger Cycloaddition: Mechanochemical Cycloelimination of a β-Lactam Mechanophore. Journal of the American Chemical Society, 137 (34). pp. 10946-10949. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20180606-113927755

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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 ^(13)C 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.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/jacs.5b07345DOIArticle
https://pubs.acs.org/doi/suppl/10.1021/jacs.5b07345PublisherSupporting Information
ORCID:
AuthorORCID
Robb, Maxwell J.0000-0002-0528-9857
Additional Information:© 2015 American Chemical Society, Received: July 14, 2015. Published: August 21, 2015. This work was supported in part by the National Science Foundation (CHE 1300313). M.J.R. gratefully acknowledges the Arnold and Mabel Beckman Foundation for a Beckman Institute Postdoctoral Fellowship. The authors declare no competing financial interest.
Funders:
Funding AgencyGrant Number
NSFCHE-1300313
Arnold and Mabel Beckman FoundationUNSPECIFIED
Issue or Number:34
Record Number:CaltechAUTHORS:20180606-113927755
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20180606-113927755
Official Citation:A Retro-Staudinger Cycloaddition: Mechanochemical Cycloelimination of a β-Lactam Mechanophore Maxwell J. Robb and Jeffrey S. Moore Journal of the American Chemical Society 2015 137 (34), 10946-10949 DOI: 10.1021/jacs.5b07345
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:86843
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:06 Jun 2018 19:51
Last Modified:03 Oct 2019 19:49

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