Mechanochemistry

Pulling for ketenes and imines

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Science  18 Sep 2015:
Vol. 349, Issue 6254, pp. 1297-1298
DOI: 10.1126/science.349.6254.1297-f

Expanding the range of reactive functional groups that can be generated by polymer mechanochemistry—literally pulling the chains apart by applying force—is important for creating new self-healing materials. Robb and Moore show that the Staudinger cycloaddition [the formation of a four-membered β-lactam ring from an imine (=N–R, where R is an alkyl or aryl group) and a ketene (=C=O)] could be reversed mechanically. Poly(methyl acrylate) polymers with an internal β-lactam ring were cleaved by ultrasonication in organic solvent. The highly reactive ketene was scavenged with isobutanol.

J. Am. Chem. Soc. 10.1021/jacs.5b07345 (2015).

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