title: Facile oxidation of primary amines to nitriles using an oxoammonium salt.
abstract: The oxidation of primary amines using a stoichiometric quantity of 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (1) in CH2Cl2-pyridine solvent at room temperature or at gentle reflux affords nitriles in good yield under mild conditions. The mechanism of the oxidation, which has been investigated computationally, involves a hydride transfer from the amine to the oxygen atom of 1 as the rate-limiting step.
authors.affiliation: Department of Chemistry, University of Connecticut , Storrs, Connecticut 06269, United States.
authors.forename: Kyle M
authors.initials: KM
authors.lastname: Lambert
authors.forename: James M
authors.initials: JM
authors.lastname: Bobbitt
authors.forename: Sherif A
authors.initials: SA
authors.lastname: Eldirany
authors.forename: Kenneth B
authors.initials: KB
authors.lastname: Wiberg
authors.forename: William F
authors.initials: WF
authors.lastname: Bailey