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Related Concept Videos

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
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Thermal Sigmatropic Reactions: Overview

Sigmatropic rearrangements are a class of pericyclic reactions in which a σ bond migrates from one part of a π system to another. These are intramolecular rearrangements where the total number of σ and π bonds remain unchanged.
Sigmatropic shifts are classified based on an order term [i, j ], where i and j indicate the number of atoms across which each end of the σ bond migrates. Below are examples of a [3,3] sigmatropic shift in 1,5-hexadiene, referred to as...
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Mechanical Taming of Hardy-Cope Rearrangements.

Matthew J Elardo1, Mariia Kuznetsova2,3, Jason D Kaff1

  • 1Department of Chemistry and Molecular Engineering and Science Institute, University of Washington, Seattle, Washington 98195, United States.

ACS Central Science
|June 29, 2026
PubMed
Summary
This summary is machine-generated.

Bullvalene molecules in polymers show force-induced rearrangements, offering direct evidence of mechanochemical reactions in soft materials. This discovery enables new force-responsive materials with advanced sensing capabilities.

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Organic Chemistry

Background:

  • Bullvalene is a fluxional molecule known for rapid [3,3] sigmatropic rearrangements.
  • Incorporation into polymers imparts force-responsive properties, but direct observation of rearrangements under stress in soft materials is challenging.
  • Previous studies lacked direct spectroscopic evidence of force-induced bullvalene isomer changes in polymers.

Purpose of the Study:

  • To provide direct spectroscopic evidence of bullvalene rearrangements in response to mechanical force within a polymer system.
  • To demonstrate bullvalene as a mechanophore capable of multiple, stimulus-independent mechanochemical reactions.
  • To explore the development of advanced force-responsive materials and macromolecular sensors.

Main Methods:

  • Utilized a polymer-chain-centered fluorinated bullvalene core.
  • Employed spectroscopic techniques to observe changes in the bullvalene isomer distribution.
  • Applied mechanical force to the polymeric system to induce and monitor rearrangements.

Main Results:

  • Direct spectroscopic evidence of bullvalene isomer distribution changes under mechanical force was obtained.
  • Confirmed the fluxional nature of bullvalene within a polymer matrix responds to applied stress.
  • Established bullvalene as the first mechanophore capable of multiple mechanochemical reactions without external triggers.

Conclusions:

  • Bullvalene's unique rearrangements under force provide a new mechanism for force-responsive materials.
  • These findings pave the way for novel materials with enhanced mechanical properties and sensing abilities.
  • The study highlights the potential of fluxional molecules in designing advanced smart materials.