Oxidative Deprotection of Oximes with Peroxodisulfate under Heterogeneous Conditions¹

Abstract

A reagent combination of (NH4)2S2O8, a catalytic amount of AgNO3, in general, or Cu(NO3)2 in particular, and moist montmorillonite K10 clay in hexane regenerates the parent carbonyl compounds in high yields under relatively mild conditions.

Update 1 of: Protection (and Deprotection) of Functional Groups in Organic Synthesis by Heterogeneous Catalysis

“…Various ammonium and metal nitrates and potassium permanganate mixed with clays were reported to regenerate carbonyl compounds from oximes and semicarbazones. – , In some cases, the reaction occurs simply by grinding all the reagents in a mortar. The same reactions can be performed in shorter times by microwave irradiation. – …”

Protection (and Deprotection) of Functional Groups in Organic Synthesis by Heterogeneous Catalysis

“…Various ammonium and metal nitrates mixed with clays were reported to regenerate carbonyl compounds from oximes and semicarbazones. − In some cases, the reaction occurs simply by grinding all the reagents in a mortar. The same reactions can be performed in shorter times by microwave irradiation. − …”

Manganese dioxide coated cotton fabric decorated with palladium nanoparticles for oxidation of alcohols, oxidative deprotection of oximes and degradation of methyl orange

“…On the other hand, protection and deprotection of carbonyl compounds constitute important processes in the synthetic organic chemistry. Oximes have been widely used as versatile carbonyl protecting groups and deprotection of oximes is a signi cant transformation (Hirano et al 2001).…”