The addition of fluorine to perhalogenated compounds containing carbon-nitrogen double bonds

The reaction of elementary fluorine with ten perhalogenated compounds containing carbon-nitrogen double bonds is reported. The reactions were carried out without added catalysts in a static system. With CF₃N=CF₂, (CF₃)₂NCF=NCF₃, SF₅N=CF₂, CF₂=NCl, CF₃CF=NCl and CF₂=NF a simple addition of fluorine to the carbon-nitrogen double bond was observed forming the respective N-fluoroamines in high yield. Two imines, CF₃CF=NF and (CF=NF)₂, were unreactive under the same conditions and reactions of CF₃CF₂CF=NF and (CF₃)₂C=NF were explosive.