Reaction of imines of fluorinated ketones and perfluoronitriles with carbon tetrachloride. A new route to polyfluorinated imines

The reaction of imines of hexafluoroacetone and 1,3-dichlorotetrafluoroacetone with CCl4 catalyzed by AlCl3 leads to the formation of (XCF2)2CClNCCl2 in moderate to high yield. The treatment of these imines with alkali metal fluoride in a polar solvent results in high yield formation of (XCF2)2CNCF3 along with isomeric (XCF2)2CFNCF2. A reaction of nitriles of perfluorinated carboxylic acids with CCl4 proceeds with the formation of a mixture of two products: RfCCl2NCCl2 and RfCCl2NCClRf. Imidoyl chloride C3F7CCl2NCClC3F7 isolated in the reaction of C3F7CN/CCl4 is converted into perfluoro-5-azanonene-4 by reaction with HF.