Syntheses of (Difluoroamino)Difluoroacetonitrile, Syn-Fluoro(Fluoroimino)Acetonitrile, and Syn-3,3,3-Trifluoro-2-(Fluoroimino)Propanenitrile and Their Reactions with Chlorine Fluoride. Syntheses of New Perfluorinated Diazines

摘要

Highly fluorinated nitrogen compounds that contain the -NF2, -NCl2-NFC1, and/or-N=N- functionalities are very reactive synthetic reagents and are potentially explosive materials. Tetrafluorohydrazine, N2F4, has had a major impact on the development of the fluoronitrogen field. Of particular interest are the reactions of N2F4 with certain olefins that when carried out the presence of an alkali-metal fluoride gave (fluoroimino)acetonitriles. The reactions of these fluoroimino nitriles and related compounds with nucleophiles have been studied in detail, with use of such species as NH3, HN3, RONa, C2H5NH2, (C2H5)2NH, and C2H5OH5. However, addition reactions to both the cyano and the >C=NF bonds in these compounds have not been stuided. Chlroine fluoride added readily across carbon-nitrogen multiple bonds; e.g., when it was added to trifluoroacetonitrile, dichloro(pentafluoroethyl)amine resulted. Such dichloro(perhalalkyl)amines are useful synthetic reagents, and many compounds of the type RfNCl2 adn RfNF2l have been prepared.