Baeyer-Villiger Rearrangement of a Substituted Pyrrole by Oxone

Joseph P Y Kao; Sukumaran Muralidharan; Peter Y Zavalij; Steven Fletcher; Fengtian Xue; Gerald M Rosen

doi:10.1016/j.tetlet.2014.04.004

Baeyer-Villiger Rearrangement of a Substituted Pyrrole by Oxone

Tetrahedron Lett. 2014 May 7;55(19):3111-3113. doi: 10.1016/j.tetlet.2014.04.004.

Authors

Joseph P Y Kao¹, Sukumaran Muralidharan², Peter Y Zavalij³, Steven Fletcher⁴, Fengtian Xue⁴, Gerald M Rosen⁵

Affiliations

¹ Center for Biomedical Engineering and Technology, University of Maryland School of Medicine, Baltimore, MD 21201, USA ; Department of Physiology, University of Maryland School of Medicine, Baltimore, MD 21201, USA ; Center for Low Frequency EPR Imaging for In Vivo Physiology, University of Maryland, Baltimore, MD 21201, USA.
² Center for Biomedical Engineering and Technology, University of Maryland School of Medicine, Baltimore, MD 21201, USA ; Department of Physiology, University of Maryland School of Medicine, Baltimore, MD 21201, USA.
³ Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA.
⁴ Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy, Baltimore, MD 21201, USA ; University of Maryland Marlene and Stewart Greenebaum Cancer Center, Baltimore, MD 21201, USA.
⁵ Center for Biomedical Engineering and Technology, University of Maryland School of Medicine, Baltimore, MD 21201, USA ; Center for Low Frequency EPR Imaging for In Vivo Physiology, University of Maryland, Baltimore, MD 21201, USA ; Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy, Baltimore, MD 21201, USA.

Abstract

Pyrroloxyls have been reported to exhibit very narrow EPR spectral lines, essential for in vivo imaging. En route to pyrroloxyls, we observed an unexpected Baeyer-Villiger rearrangement, leading to loss of aromaticity and formation of a 4,5-dihydro-1H-ketopyrrole.

Keywords: Baeyer-Villiger; Vilsmeier-Haack; pyrrole; pyrroloxyl.

Abstract

Grants and funding