The Journal of organic chemistry

Surface-Mediated Reactions. 9. Selective Oxidation of Primary and Secondary Amines to Hydroxylamines1

JD Fields, PJ Kropp

Index: Fields, John D.; Kropp, Paul J. Journal of Organic Chemistry, 2000 , vol. 65, # 19 p. 5937 - 5941

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Citation Number: 69

Abstract

OXONE over silica gel or, in some cases, alumina has been found to oxidize the primary and secondary amines 3 selectively to the corresponding hydroxylamines 4, in either the presence or absence of a solvent. Treatment of Boc-protected l-lysine (6) under the latter conditions afforded hydroxylamine 7 in excellent yield. The trialkylamine 1a and pyridine (1b), in which selectivity is not an issue, were readily oxidized to the corresponding oxides ...