Defluorination and Other Transformations of Perfluorinated Tetralin, Alkyltetralins and 4-Methyl-1,2-dihydronaphthalene in the System Zn–DMF. Synthesis of Perfluoro-1-ethyl- and -1-methylnaphthalenes

Abstract

The reaction of perfluorotetralin with zinc in DMF, followed by treatment with water, gave 1,1,2,2,3,3,4,4,5,6,8-undecafluorotetralin, perfluoro-2,2′-binaphthalene, and octafluoronaphthalene. Under similar conditions, perfluoro-1-ethyltetralin was converted into a mixture of 1,2,3,4,6,7-hexafluoro-5-(per­fluoro­ethyl)naphthalene and perfluorinated 1-ethyl- and 1-vinylnaphthalenes, perfluoro-6-methyltetralin gave rise to 1,2,4,5,6,8-hexafluoro-3-(trifluoromethyl)naphthalene and perfluoro-2-methylnaphthalene, and per­fluoro-1-methylnaphthalene was obtained from perfluoro-4-methyl-1,2-dihydronaphthalene. Perfluoro-1-ethyl­tetralin reacted with bromine-activated zinc in DMF to produce a mixture containing (perfluoro-4-ethylnaph­thalen-1-yl)zinc bromide which was converted to 1,2,3,4,6,7-hexafluoro-5-(perfluoroethyl)naphthalene by the action of water, while its reaction with CuCl₂ afforded perfluoro-4,4′-diethyl-1,1′-binaphthalene.