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Baeyer–Villiger rearrangement of a substituted pyrrole by Oxone
Authors:Joseph PY Kao  Sukumaran Muralidharan  Peter Y Zavalij  Steven Fletcher  Fengtian Xue  Gerald M Rosen
Institution:1. Center for Biomedical Engineering and Technology, University of Maryland School of Medicine, 20 North Pine Street, Baltimore, MD 21201, USA;2. Department of Physiology, University of Maryland School of Medicine, 20 North Pine Street, Baltimore, MD 21201, USA;3. Center for Low Frequency EPR Imaging for In Vivo Physiology, University of Maryland, Baltimore, MD 21201, USA;4. Department of Chemistry and Biochemistry, University of Maryland, College Park, MD 20742, USA;5. Department of Pharmaceutical Sciences, University of Maryland School of Pharmacy, Baltimore, MD 21201, USA;6. University of Maryland Marlene and Stewart Greenebaum Cancer Center, 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:Pyrrole  Pyrroloxyl  Vilsmeier&ndash  Haack  Baeyer&ndash  Villiger
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