Ketone Regeneration from Oximes with Alkaline Hydrogen Peroxide

Abstract

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.