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Force-Accelerated Ring Opening of Episulfide by Pulsed Ultrasonication
Chun-Hao Ko1,2, Hsi-Chih Wang1,2, Van-Sieu Luc1,3,4
1Department of Applied Chemistry, National Yang Ming Chiao Tung University, Hsinchu 300093, Taiwan.
Macromolecules
|March 2, 2026
Summary
Polymer mechanochemistry uses mechanical force to alter chemical reactions. This study shows alkyl and phenyl episulfides react under ultrasonication, unlike ester episulfides, enabling new transformations.
Area of Science:
- Polymer Science
- Organic Chemistry
- Mechanochemistry
Background:
- Covalent polymer mechanochemistry is an emerging field.
- Mechanical force can influence reaction pathways and stereoselectivity.
- Episulfides are strained cyclic compounds with potential for ring-opening reactions.
Purpose of the Study:
- To investigate the mechanochemical reactivity of episulfides with different substituents.
- To explore the influence of mechanical force on episulfide ring-opening reactions.
- To understand the role of substituents in dictating mechanochemical outcomes.
Main Methods:
- Pulsed ultrasonication was used to apply mechanical force to episulfides.
- Episulfides with alkyl, ester, and phenyl substituents were synthesized and studied.
- Reaction products and intermediates were analyzed to determine reactivity.
Main Results:
- Episulfides with alkyl and phenyl substituents underwent C-C bond cleavage under ultrasonication.
- Reactive intermediates were formed, leading to cis-trans isomerization and cycloaddition reactions.
- Episulfides with ester substituents were found to be mechanochemically inactive.
Conclusions:
- Mechanical force can selectively activate certain episulfide derivatives for specific chemical transformations.
- The nature of the substituent significantly impacts the mechanochemical reactivity of episulfides.
- This work highlights the potential of polymer mechanochemistry for controlling chemical reactions.
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