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EPR support for the ketyl radical-anion "triggered" [3,3]-sigmatropic rearrangement
Eric J Enholm1, Merle A Battiste, Maria Gallagher
1Department of Chemistry, University of Florida, Gainesville, Florida 32611, USA. enholm@chem.ufl.edu
The Journal of Organic Chemistry
|August 31, 2002
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.