Reactions of Trifluoroamine Oxide: A Route to Acyclic and Cyclic Fluoroamines and N-Nitrosoamines

Abstract

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 PFS, 2,2,6,6-(CH3)4-c-C5H6NF gave [CH2CH2CH2C(CH3)2N+=C(CH3)2]PF6-. © 1990, American Chemical Society. All rights reserved.