Reactions of trifluoroamine oxide: A route to acyclic and cyclic fluoroamines and N-nitrosoamines

Article abstract of DOI:10.1021/ja00162a045

Acyclic secondary fluoroamines and N-nitrosoamines R₂NF and R₂NNO (R = CH₃, C₂H₅, n-C₃H₇, i-C₃H₇, n-C₄H₉, i-C₄H₉, c-C₆H₁₁) and saturated nonaromatic heterocyclic fluoroamines and N-nitrosoamines R NF and R NNO [R = c-C₄H₈, c-C₅H₁₀, 2,6-(CH₃)₂-c-C₅H₈, 2,2,6,6-(CH₃)₄-c-C₅H₆] were prepared by reacting trifluoroamine oxide (NF₃O) with the respective amine at ≤0 °C in a 1:2 molar ratio. The amine hydrofluoride salts are also formed. Trifluoroamine oxide is a very effective fluorinating and nitrosating reagent and provides an excellent route to >NF- and >NNO-containing compounds. With PF₅, 2,2,6,6-(CH₃)₄-c-C₅H₆NFgave [CH₂CH₂CH₂C(CH₃)₂N ⁺=C(CH₃)₂]PF₆^-.