Novel Oxidation Reaction of Tertiary Amines with Osmium Tetroxide

Abstract

Tertiary amines were oxidized with OsO4 to afford mixtures of lactams, hydroxylactams, and ketolactams. In contrast to RuO4, which was known to oxidize tertiary amines, amides, and N-carbamoylamines, OsO4 oxidized the tertiary amines exclusively and tolerated amides and N-carbamoylamines. A mechanism for the oxidation reaction is also proposed.