Aromatic polyfluoro-compounds. Part XXXI. The synthesis and reactions of some halogenomethylpentafluorophenylmethanols and routes to some pentafluorophenylacetylenes

Abstract

Pentafluorophenylmagnesium bromide reacted with trichloro-, dichloro-, chlorodifluoro-, bromo-, and trifluoro-acetaldhyde to form the corresponding halogenomethylpentafluorophenylmethanols. These alcohols on oxidation afforded ketones, which underwent haloform cleavage, whilst with phosphorus pentachloride they gave the expected chloropentafluorophenylethanes in good yield. Dehydrohalogenation or dehalogenation of the latter provided routes to pentafluorophenyl- and chloropentafluorophenyl-acetylene.