International Journal of Chemical Kinetics p. 381 - 385 (1999)
Update date:2022-08-29
Topics:
Zauche, Timothy H.
Espenson, James H.
The reactions of 4-hydroxy-2,2,6,6-tetramethylpiperidinium N-oxide, an oxammonium ion abbreviated R2NO+, have been studied. The previously unreported triflate salt was used in this study because the anions of the usual chloride and bromide salts can themselves be oxidized. Reactions between R2NO+ and alcohols produce ketones and aldehydes; the rate constant for PhCH2OH is 4.4×10-3 L mol-1 s-1 in acetonitrile at 298 K. The immediate product is the hydroxylamine, R2NOH, but its further comproportionation reaction with R2NO+ yields the stable piperidinyl oxyl radical, R2NO·. The rate constant of this reaction is 1.78×103 L mol-1 s-1 at 298 K. The possibility of using R2NO+ and MTO as co-catalysts for the oxidation of alcohols was explored, but the competitive rates are such that the resultant is not particularly attractive.
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