| Abstract: | 4-Amino-2,2,5,5-tetrakis(trifluoromethyl)-3-oxazoline ( 3a ) was prepared from the reaction of sodium cyanide with hexafluoroacetone and hexafluoroacetone imine, and from the reaction of hexafluoroacetone cyanohydrin with the imine. Several other oxazolines were also prepared by related reactions of other fluoroketones and imines. The proton nmr spectrum of an 15N-labeled sample of 3a shows that it exists in solution primarily as the amino tautomer and not as the imino tautomer 3b . Comparison of 3a with the closely related, pharmacologically active 4-amino-2,2,5,5-tetrakis(trifluoromethyl)-3-imidazoline ( 2 ) has shown large differences in ΔH of complex formation and reactivity with electrophilic reagents. |
