A Novel SN1 Displacement: The Reaction of Tertiary Amines with Acetic Anhydride

Abstract

The action of actic anhydride on tertiary amines at reflux may cause the displacement of one of the R groups from the amine. The groups which are displaced are benzyl, t-butyl, benzhydryl, trityl, and cinnamyl; the groups which are not displaced are methyl, ethyl, n-butyl, phenyl, α-naphthyl, iso-propyl, allyl, and propargyl. An SN1 mechanism with special steric requirements is consistent with the experimental results.