Selective oxidations by nitrosating agents

Selective oxidations by nitrous acid in aqueous sulfuric acid towards alklyl side chains of enolizable ketones are reported. For instance, the oxidation of acetophenone to benzoylformic acid occurs in high yields (>95%) at 25 °C in the narrow acidity range 72-80% of sulphuric acid concentration. Details of the process between enolizable ketones and electrophilic species in concentrated aqueous acid solutions are also discussed.