Accelerating a Mechanically Driven anti-Woodward-Hoffmann Ring Opening with a Polymer Lever Arm Effect.
Publication
, Journal Article
Wang, J; Kouznetsova, TB; Niu, Z; Rheingold, AL; Craig, SL
Published in: The Journal of organic chemistry
December 2015
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 benzocyclobutene (BCB). Addition of an α-E-alkene to the BCB mechanophore drops the force required to induce reactions on the ∼0.1 s time scale of single-molecule force spectroscopy experiments from 1370 to 920 pN.
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Published In
The Journal of organic chemistry
DOI
EISSN
1520-6904
ISSN
0022-3263
Publication Date
December 2015
Volume
80
Issue
23
Start / End Page
11895 / 11898
Related Subject Headings
- Organic Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry
Citation
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NLM
Wang, J., Kouznetsova, T. B., Niu, Z., Rheingold, A. L., & Craig, S. L. (2015). Accelerating a Mechanically Driven anti-Woodward-Hoffmann Ring Opening with a Polymer Lever Arm Effect. The Journal of Organic Chemistry, 80(23), 11895–11898. https://doi.org/10.1021/acs.joc.5b01465
Wang, Junpeng, Tatiana B. Kouznetsova, Zhenbin Niu, Arnold L. Rheingold, and Stephen L. Craig. “Accelerating a Mechanically Driven anti-Woodward-Hoffmann Ring Opening with a Polymer Lever Arm Effect.” The Journal of Organic Chemistry 80, no. 23 (December 2015): 11895–98. https://doi.org/10.1021/acs.joc.5b01465.
Wang J, Kouznetsova TB, Niu Z, Rheingold AL, Craig SL. Accelerating a Mechanically Driven anti-Woodward-Hoffmann Ring Opening with a Polymer Lever Arm Effect. The Journal of organic chemistry. 2015 Dec;80(23):11895–8.
Wang, Junpeng, et al. “Accelerating a Mechanically Driven anti-Woodward-Hoffmann Ring Opening with a Polymer Lever Arm Effect.” The Journal of Organic Chemistry, vol. 80, no. 23, Dec. 2015, pp. 11895–98. Epmc, doi:10.1021/acs.joc.5b01465.
Wang J, Kouznetsova TB, Niu Z, Rheingold AL, Craig SL. Accelerating a Mechanically Driven anti-Woodward-Hoffmann Ring Opening with a Polymer Lever Arm Effect. The Journal of organic chemistry. 2015 Dec;80(23):11895–11898.
Published In
The Journal of organic chemistry
DOI
EISSN
1520-6904
ISSN
0022-3263
Publication Date
December 2015
Volume
80
Issue
23
Start / End Page
11895 / 11898
Related Subject Headings
- Organic Chemistry
- 3405 Organic chemistry
- 3404 Medicinal and biomolecular chemistry
- 0305 Organic Chemistry
- 0304 Medicinal and Biomolecular Chemistry