A Retro-Staudinger Cycloaddition: Mechanochemical Cycloelimination of a 尾-Lactam Mechanophore
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- 作者：Maxwell J. Robb ; Jeffrey S. Moore
- 刊名：Journal of the American Chemical Society
- 出版年：2015
- 出版时间：September 2, 2015
- 年：2015
- 卷：137
- 期：34
- 页码：10946-10949
- 全文大小：336K
- ISSN：1520-5126
文摘
Mechanical activation of a 尾-lactam mechanophore using ultrasound induces a formal [2 + 2] cycloelimination reaction producing ketene and imine functional groups鈥攖he reverse reaction of the Staudinger cycloaddition. This transformation is predicted by computational modeling and verified by kinetics and UV鈥搗is absorption measurements as well as polymer end-group analysis using 1H and 13C NMR spectroscopy. Addition of the 尾-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.