Cleavage of Oximes, Semicarbazones, and Phenylhydrazones with Supported Potassium Permanganate

Abstract

Potassium permanganate supported on manganese(II) sulfate or activated manganese dioxide can be used effectively for the oxidative cleavage of oximes and semicarbazones under solvent-free conditions and for the cleavage of phenylhydrazones in dichloromethane. The residue that remains after extraction of the organic products, primarily manganese oxides, can be recycled, making the process, in theory, infinitely sustainable.

SnCl2/TiCl3-Mediated Deoximation of Oximes in an Aqueous Solvent

“…A plethora of examples of procedures for the regeneration of carbonyl compounds from oximes have been reported. So far a good number of deoximation methods based on hydrolytic [7], reductive [8,9,10,11,12], oxidative [13,14,15,16,17,18,19], and transoximation [20,21,22] reactions have been developed. Among them some require strong acidic conditions; some take long reaction times, and give low product yields, while some are performed at higher temperatures.…”

Mild Oxidation of Oxime Derivatives with KMnO4 in Ionic Liquid Media

“…Several oxidative methods have been developed for deoximination in the literature. [3][4][5][6][7][8][9][10][11] However, some of these methods suffer from disadvantages such as long reaction times, low yields of the product and tedious work up. There has been considerable interest in the use of selective and cleaner oxidation methods such as heterogeneous oxidation and oxidation in ionic liquids in recent years.…”