Pulling versus heating

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Science  08 Dec 2017:
Vol. 358, Issue 6368, pp. 1267-1268
DOI: 10.1126/science.358.6368.1267-g

Mechanical force can activate and break bonds in ways that differ from thermal mechanisms or photoactivation. Stevenson and De Bo studied the effects of substituent positions on retro-Diels-Alder reactions in which a bridged ring opened to form substituted furans and maleimides. Thermal activation depended on stereochemistry (endo or exo configurations), but mechanochemistry (activating the molecule with ultrasound) depended instead on regiochemistry (proximal or distal geometries). The thermally reactive distal-exo adduct was unreactive in the ultrasound experiments.

J. Am. Chem. Soc. 10.1021/jacs.7b08895 (2017).

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