Reinvestigating the Role of Multiple Hydrogen Transfers in Baeyer−Villiger Reactions
2007; American Chemical Society; Volume: 72; Issue: 17 Linguagem: Inglês
10.1021/jo070956t
ISSN1520-6904
AutoresJ. Raúl Alvarez‐Idaboy, Lino Reyes,
Tópico(s)Surface Chemistry and Catalysis
ResumoA comparison between a tetramolecular mechanism (J. Org. Chem. 2007, 72, 3031) and our previously proposed mechanism has been performed. The results show that the tetramolecular mechanism is less favored in terms of Gibbs free energy, and therefore, the reaction in acidic media is acid catalyzed. The role of the catalyst in the migration step has been corrected and discussed. A new transition state is proposed for this step. The change in the rate-determining step for the cyclohexanone + performic acid reaction supports our results.
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