Conversions of primary amines to azides by n-butyllithium and azidotris(diethylamino)phosphonium bromide

Lithium derivatives of varied aromatic, heterocyclic, aliphatic, and alicyclic primary amines react efficiently with azidotris(diethylamino)phosphonium bromide in THF at low temperatures to give azides, lithium bromide, nitrogen, and tris(diethylamino)phosphorimine.