1‐Methylimidazolium chlorochromate: A new Cr(VI) oxidant and use of anhydrous acetic acid as the catalyst for the oxidation of primary and secondary alcohols

Abstract

The synthetic potential of a new Cr(VI) reagent, viz., 1‐methylimidazolium chlorochromate, analogous to Corey's reagent‐PCC, has been examined. Anhydrous acetic acid has been found to catalyze the oxidation reaction.

N-Chloro-3-methyl-2,6-diphenylpiperidin- 4-one (NCP) – An Efficient, Mild, Stable Oxidant for Cleavage of Carbon-Nitrogen Double Bonds of Oximes

“…There are several methods for regeneration of carbonyl compounds from oximes, such as manganese triacetate, [2] dinitrogentetroxide, [3] titanium silicate, [4] ammonium persulfate-silicagel, [5] tetrabutyl ammonium persulfate, [6] zirconium sulfophenyl phosphonate, [7] zinc bismuthate, [8] sodium perborate, [9] iodine, [10] sodium periodate, [11] Dess-Martin periodinane, [12] raney nickel, [13] chromiumtrioxide-silicagel-microwave, [14] ferric chloride-silicagel, [15] bismuth trichloride, [16] trimethylsilylchlorochromate, [17] triethylammonium chlorochromate, [18] pyridinium chlorochromate-microwave, [19] methylammonium chlorochromate-alumina [20] and halochromates prepared from quinoline, [21] 2,2 0 bipyridine, [22] imidazole, [23] and 1-methyl imidazole. [24] However many of these methods do not describe the deoximation of aldoximes or give low yields or the liberated aldehydes are over oxidized. Moreover, the reagents used are often hazardous or toxic and having expensive transition metals.…”