Nitrogen inversion in alkyldifluoroamines

Abstract

The temperature- and solvent-dependence of nitrogen inversion in several bis-(NN-difluoroamino)alkanes has been investigated by ¹⁹F n.m.r. spectroscopy. The rates of nitrogen inversion are measurably slow on the fluorine n.m.r. time scale at room temperature or below; the pyramidal stability of the secondary alkyldifluoroamino-group in 2-methyl-2,3-bis-(NN-difluoroamino)butane is the greatest yet found for an acyclic amine. For many of the examples, meaningful kinetic data could not be obtained. The reasons are discussed.