EPR support for the ketyl radical-anion "triggered" [3,3]-sigmatropic rearrangement.
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.
Enholm
Eric J
EJ
Department of Chemistry, University of Florida, Gainesville, Florida 32611, USA. enholm@chem.ufl.edu
Battiste
Merle A
MA
Gallagher
Maria
M
Moran
Kelley M
KM
Alberti
Angelo
A
Guerra
Maurizio
M
Macciantelli
Dante
D