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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Mechanogeneration of Acid from Oxime Sulfonates
Chikkannagari Nagamani1, Huiying Liu1, Jeffrey S Moore1
1Department of Chemistry and ¶Beckman Institute for Advanced Science and Technology, University of Illinois at Urbana-Champaign , Urbana, Illinois 61801, United States.
Abstract:
The generation of acid under mechanical force is potentially useful for initiating proton-catalyzed changes in polymeric materials. Here we demonstrate that oxime sulfonates-known photoacid generators-are also acid generators when activated mechanically. NMR analysis of products suggests that the ultrasound-induced mechanochemical scission of the oxime sulfonate mechanophore also generates a ketone functional moiety, in addition to acid. Both acid and ketone moieties are useful for developing stress-responsive polymeric materials for autonomous self-healing applications.
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