Preparation of N-aryl-ketonitrone spin traps

The syntheses of seven N-aryl-C,C-dialkoxycarbonylnitrones 1–7, six of which were original, were achieved from the appropriate aryl-nitroso compounds. These ketonitrones were found to trap efficiently carbon-centred free radicals in aqueous media, yielding stable aminoxyl radicals whose EPR spectra lasted several days. The two penta-deuterated compounds 6 and 7 were also found to be efficient at trapping methoxyl radical. Their various spin adducts showed simple three line signals, very sensitive to the polarity of the environment. This study represents the very first use of linear ketonitrones as spin traps.