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EPR support for the ketyl radical-anion "triggered" [3,3]-sigmatropic rearrangement
Authors:Enholm Eric J  Battiste Merle A  Gallagher Maria  Moran Kelley M  Alberti Angelo  Guerra Maurizio  Macciantelli Dante
Affiliation:Department of Chemistry, University of Florida, Gainesville, Florida 32611, USA. enholm@chem.ufl.edu
Abstract:New physical evidence to support a ketyl radical-anion mechanism for the [3,3]-sigmatropic rearrangement is presented. With use of EPR spectroscopy, spectra are observed that can be attributed to 8, an acyl radical-anion species resulting from a [3,3]-rearrangement; this also functions as a key intermediate in the process. The spectrum of an additional paramagnetic species resulting from further addition of tin-centered radicals to the reaction product was also observed.
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