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  Synergistic Effect of Ketone and Hydroperoxide in Brønsted Acid Catalyzed Oxidative Coupling Reactions

Schweitzer-Chaput, B., Sud, A., Pintér, Á., Dehn, S., Schulze, P., & Klussmann, M. (2013). Synergistic Effect of Ketone and Hydroperoxide in Brønsted Acid Catalyzed Oxidative Coupling Reactions. Angewandte Chemie International Edition, 52(50), 13228-13232. doi:10.1002/anie.201306752.

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anie_201306752_sm_miscellaneous_information.pdf (Supplementary material), 2MB
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anie_201306752_sm_miscellaneous_information.pdf
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Supporting Information
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Public
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application/pdf / [MD5]
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Copyright Date:
2013
Copyright Info:
Wiley-VCH 69451 Weinheim, Germany
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 Creators:
Schweitzer-Chaput, Bertrand1, Author           
Sud, Abhishek1, Author           
Pintér, Áron1, Author           
Dehn, Stefanie2, Author           
Schulze, Philipp2, Author           
Klussmann, Martin1, Author           
Affiliations:
1Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445608              
2Service Department Schulze (GC, HPLC), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_persistent22              

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Free keywords: autoxidation; organocatalysis; oxidative coupling; peroxides; reaction mechanisms
 Abstract: Waste not wasted: A mechanistic study of the autoxidative coupling of xanthene with cyclopentanone uncovered an autoinductive effect of the waste product hydrogen peroxide. It generates radicals in the presence of acid and ketones, which accelerate the reaction by providing an additional pathway to the reactive hydroperoxide intermediate. This discovery could be applied to achieve other Brønsted acid-catalyzed oxidative coupling reactions.

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Language(s): eng - English
 Dates: 2013-08-012013-10-222013-12-09
 Publication Status: Published in print
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.201306752
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 52 (50) Sequence Number: - Start / End Page: 13228 - 13232 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851