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Acid-Catalyzed Activation of Peroxyketals: Tunable Radical Initiation at Ambient Temperature and Below

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Schweitzer-Chaput,  Bertrand
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Böß,  Esther
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Klußmann,  Martin
Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Schweitzer-Chaput, B., Böß, E., & Klußmann, M. (2016). Acid-Catalyzed Activation of Peroxyketals: Tunable Radical Initiation at Ambient Temperature and Below. Organic Letters, 18(19), 4944-4947. doi:10.1021/acs.orglett.6b02419.


Cite as: https://hdl.handle.net/11858/00-001M-0000-002B-A004-F
Abstract
This study details how peroxyketals, commercially available thermal initiators, and structurally related peroxides are activated in the presence of an acid catalyst to generate radicals at room temperature and below. This simple combination of two substrates was shown to efficiently initiate a variety of radical processes. This phenomenon is rationalized by the acid-catalyzed in situ formation of highly unstable alkenyl peroxides which readily decompose into initiating radical species.