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  Acid-Mediated Formation of Radicals or Baeyer-Villiger Oxidation from Criegee Adducts

Schweitzer-Chaput, B., Kurtén, T., & Klussmann, M. (2015). Acid-Mediated Formation of Radicals or Baeyer-Villiger Oxidation from Criegee Adducts. Angewandte Chemie International Edition, 54(40), 11848-11851. doi:10.1002/anie.201505648.

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 Creators:
Schweitzer-Chaput, Bertrand1, Author              
Kurtén, Theo2, Author
Klussmann, Martin1, Author              
Affiliations:
1Research Group Klußmann, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445608              
2University of Helsinky, ou_persistent22              

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Free keywords: TERT-BUTYL HYDROPEROXIDE; PEROXIDES; OZONOLYSIS; KETONES; REARRANGEMENT; ABSTRACTION; CATALYSIS; PRODUCTS; OLEFINS; ACETONEChemistry; Baeyer-Villiger oxidation; Bronsted acid catalysis; ketones; peroxides; radical reactions;
 Abstract: The acid-mediated reaction of ketones with generates radicals, a process with reaction conditions similar to those of the Baeyer-Villiger oxidation but with an outcome resembling the formation of hydroxyl radicals via ozonolysis in the atmosphere. The Baeyer-Villiger oxidation forms esters from ketones, with the preferred use of peracids. In contrast, alkyl hydroperoxides and hydrogen peroxide react with ketones by condensation to form alkenyl peroxides, which rapidly undergo homolytic O-O bond cleavage to form radicals. Both reactions are believed to proceed via Criegee adducts, but the electronic nature of the peroxide residue determines the subsequent reaction pathways. DFT calculations and experimental results support the idea that, unlike previously assumed, the Baeyer-Villiger reaction is not intrinsically difficult with alkyl hydroperoxides and hydrogen peroxide but rather that the alternative radical formation is increasingly favored.

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Language(s): eng - English
 Dates: 2015-09-28
 Publication Status: Published in print
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: ISI: 000363394800047
DOI: 10.1002/anie.201505648
 Degree: -

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Title: Angewandte Chemie International Edition
  Other : Angew. Chem., Int. Ed.
  Other : Angew. Chem. Int. Ed.
  Other : Angewandte Chemie, International Edition
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: 40 Volume / Issue: 54 (40) Sequence Number: - Start / End Page: 11848 - 11851 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851