Oxoammonium salts. 6. 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium perchlorate: A stable and convenient reagent for the oxidation of alcohols. Silica gel catalysis
Jm. Bobbitt, Oxoammonium salts. 6. 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium perchlorate: A stable and convenient reagent for the oxidation of alcohols. Silica gel catalysis, J ORG CHEM, 63(25), 1998, pp. 9367-9374
4-Acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium perchlorate, 1, i
s a stable, nonhygroscopic oxoammonium salt that is easily prepared and can
be used for the oxidation of alcohols to ketones or aldehydes in near quan
titative yields. The reaction is colorimetric, does not require anhydrous c
onditions, does not involve heavy metals, and can be carried out convenient
ly. Furthermore, the oxidant can be easily regenerated. The oxidation is so
mewhat specific in that the relative reactivities of an allyl alcohol (gera
niol), benzaldehyde, and 1-decanol are about 100: 1:0.1. The reaction is ca
talyzed by silica gel.