The reaction of lead tetra-acetate with oximes. Part I. Alicyclic and aliphatic oximes

Stable free radicals obtained by the action of lead tetra-acetate on the oximes of cyclopentanone, cyclohexanone, 4-butylcyclohexanone, acetone, heptan-2-one, and heptan-4-one are tentatively assigned structures corresponding to the addition of two acetoxy groups to the CN bond of the oximes, and are characterised by their electron paramagnetic resonance (e.p.r.) spectra. The corresponding acetoxy-nitroso radical anions have been generated separately and characterised by e.p.r. There is a configurational effect on the nitrogen hyperfine coupling of the radical anion derived from 1-acetoxy-1-nitroso-4-t-butylcyclohexane. Evidence is provided for the existence of two concurrent reactions between lead tetra-acetate and oximes.