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Do α-acyloxy and α-alkoxycarbonyloxy radicals fragment to form acyl and alkoxycarbonyl radicals?

Authors
  • Dennis P Curran
  • Tiffany R Turner
Publisher
BioMed Central
Publication Date
May 25, 2006
Source
PMC
Keywords
License
Unknown

Abstract

The generation of α-acyloxy and α-alkoxycarbonyloxy radicals under reductive conditions in fragmentable probe experiments does not provide unequivocal evidence for the fragmentation of such radicals to give ketones and acyl or alkoxycarbonyl radicals. Instead, standard reduction predominates, even at low tin hydride concentrations. Some ketone product is formed in the α-acyloxy substrate at low concentrations, but it is unclear whether this product arises through a slow radical fragmentation process or an inefficient, chain-breaking oxidative process.

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