DEHYDROFLUORINATION OF ALKYLDIFLUORAMINES

Kinetics of dehydrofluorination of several mono-, bis-, and tris(N,N-difluoramino)alkanes have been measured in diglyme-water (30:70) at 50 and 75°. The rates of these imine-forming reactions are relatively insensitive to the inductive and conjugative effects of substituents; the stereoselectivity of the dehydrofluorination seems to reflect the steric requirements of the alkyl group. The elimination appears to be a concerted process in which the degree of N-F bond breaking is not only quite extensive, but also nearly equal to the degree of C-H bond breaking in the transition state. All of the dehydrofluorination products have been fully characterized. © 1969, American Chemical Society. All rights reserved.