Stanislav Grabovskiy - Base-Promoted Reaction of 5-Hydroxyuracil Derivatives with Peroxyl Radicals

Version 2

      Publication Details (including relevant citation   information):

      Org. Lett., 2010,   12 (18), pp 4130–4133
      DOI: 10.1021/ol1017245

      Abstract:

      Addition of millimolar amounts of a weak base (pyridines)   dramatically accelerates the reaction with peroxyl radicals of   two biologically relevant uracil derivatives, 5-hydroxyuracil   (HU) and 5-hydroxy-6-methyluracil (HMU). This is due to the   formation of small amounts of the deprotonated form   (pKa = 8.1−8.5 in water), which reacts with   peroxyl radicals much faster than the parent undissociated form,   via formal H-atom transfer from the OH in the 5 position.

      Address (URL): http://pubs.acs.org/doi/abs/10.1021/ol1017245