Oxoammonium Salts. 6.¹ 4-Acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium Perchlorate:  A Stable and Convenient Reagent for the Oxidation of Alcohols. Silica Gel Catalysis

Abstract

4-Acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium perchlorate, 1, is a stable, nonhygroscopic oxoammonium salt that is easily prepared and can be used for the oxidation of alcohols to ketones or aldehydes in near quantitative yields. The reaction is colorimetric, does not require anhydrous conditions, does not involve heavy metals, and can be carried out conveniently. Furthermore, the oxidant can be easily regenerated. The oxidation is somewhat specific in that the relative reactivities of an allyl alcohol (geraniol), benzaldehyde, and 1-decanol are about 100:1:0.1. The reaction is catalyzed by silica gel.