Ketone Regeneration from Oximes with Alkaline Hydrogen Peroxide

In our recent work a practical method for regenerating acid-sensitive ketones from the corresponding oximes was needed. While hydrolysis in hydrochloric acid, either alone or with added hydroxylamine interceptors (formaldehyde,1 pyruvic acid,2 levulinic acid,3 etc.) was precluded, the use of various oxidizing [Pb (IV),4 Cu (II),4 Hg (II),4 Ce (IV),4,5 Cr (VI),4,6 Tl (III),7 I (VII)4, 6] or reducing [Cr (II),8 Ti (III),9 Mo (III),10 Zn,11 Fe(CO)5 12] agents was also deemed unsuitable, for economic and pollution reasons. The presence of olefinic linkages in our substrates further limited such reagents as ozone.13 These constraints led us to consider other ways to achieve oxidative deoximation.