Arylazopolyfluoroalkenes from terminal perfluoroolefins

The reactions of perfluoro-1-hexene and perfluoro-1-butene with phenylhydrazine givs phenylhydrazones of acid fluoride derivatives of the corresponding polyfluorocarboxylic acids. The dehydrofluorination of these products using triethylamine gives conjugated arylazopolyfluoroalkenes. The dehydrofluorination of the phenylhydrazone of a-hydroperfluorocaproyl fluoride by the action of phenylhydrazine leads to the phenylhydrazone of perfluoro-2-pentenoyl fluoride (IV).