Reinvestigation of Acetophenones Oxidation by Performic Acid in Formic Acid

The Journal of Physical Chemistry. a
Lino ReyesJ Raúl Alvarez-Idaboy

Abstract

The Baeyer-Villiger (BV) reaction of acetophenones R-COCH3 (R = phenyl, 4-methylphenyl, 3,4-dimethoxyphenyl) with performic acid (PFA) in formic acid (FA) as the catalyst and solvent was reinvestigated using the MPWB1K functional in conjunction with the 6-311G(d,p) and 6-311++G(d,p) basis sets. For the acid-catalyzed addition step, we used the eight-membered ring transition structure proposed in our previous work. The calculated and experimental results obtained for the BV reaction under the mentioned conditions lead to the conclusion that our mechanism is more reliable than the one reported by Liu and co-workers, in which the acid-catalyzed first step involves a transition state with a six-membered ring structure.

References

Apr 21, 2001·The Journal of Organic Chemistry·P CarlqvistT Brinck
Sep 9, 2004·Chemical Reviews·G-J ten BrinkR A Sheldon
Oct 9, 2004·The Journal of Organic Chemistry·Michelle SnowdenJennifer L Radkiewicz-Poutsma
Jul 13, 2006·The Journal of Physical Chemistry. a·Lino ReyesManuel Rubio
Jul 28, 2007·The Journal of Organic Chemistry·J Raul Alvarez-Idaboy, Lino Reyes
Nov 1, 2007·Organic & Biomolecular Chemistry·J Raul Alvarez-IdaboyNelaine Mora-Diez
Aug 27, 2009·Organic & Biomolecular Chemistry·Nelaine Mora-DiezJ Raúl Alvarez-Idaboy
Feb 24, 2012·The Journal of Physical Chemistry. a·Bo LiuChang-Wei Hu

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