Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 23, Pages 11895-11898Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01465
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Funding
- National Science Foundation [CHE-1508566]
- NSF Research Triangle MRSEC [DMR-1121107]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1508566] Funding Source: National Science Foundation
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Mechanical forces have previously been used to drive reactions along pathways that violate the orbital symmetry effects captured in the Woodward-Hoffmann rules. Here, we show that a polymer lever arm effect can provide a mechanical advantage in accelerating the symmetry forbidden disrotatory ring opening of benzocydobutene (BCB). Addition of an alpha-E-alkene to the BCB mechanophore drops the force required to induce reactions on the similar to 0.1 s time scale of single-molecule force spectroscopy experiments from 1370 to 920 pN.
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