Accelerating a Mechanically Driven anti-Woodward-Hoffmann Ring Opening with a Polymer Lever Arm Effect.

Journal Article

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.

Full Text

Duke Authors

Cited Authors

  • Wang, J; Kouznetsova, TB; Niu, Z; Rheingold, AL; Craig, SL

Published Date

  • December 2015

Published In

Volume / Issue

  • 80 / 23

Start / End Page

  • 11895 - 11898

PubMed ID

  • 26270991

Electronic International Standard Serial Number (EISSN)

  • 1520-6904

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/acs.joc.5b01465

Language

  • eng