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

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The reaction of imines of hexafluoroacetone and 1,3-dichlorotetrafluoroacetone with CCl 4 catalyzed by AlCl 3 leads to the formation of (XCF 2) 2CClNCCl 2 in moderate to high yield. The treatment of these imines with alkali metal fluoride in a polar solvent results in high yield formation of (XCF 2) 2CNCF 3 along with isomeric (XCF 2) 2CFNCF 2. A reaction of nitriles of perfluorinated carboxylic acids with CCl 4 proceeds with the formation of a mixture of two products: R fCCl 2NCCl 2 and R fCCl 2NCClR f. Imidoyl chloride C 3F 7CCl 2NCClC 3F 7 isolated in the reaction of C 3F 7CN/CCl 4 is converted into perfluoro-5-azanonene-4 by reaction with HF.