Studies in azide chemistry. Part III. Polyfluorinated azides from 1H-and 2H-pentafluoropropene and perfluorobut-2-yne

Abstract

Treatment of 1H-pentafluoropropene with sodium azide in dimethylformamide gave 1H-tetrafluoroprop-1-enyl azide; this product was also obtained, together with a compound tentatively identified as 1H,2H-pentafluoropropyl azide, when 1H-pentafluoropropene was treated with triethylammonium azide in sym-tetrachloroethane. The occurrence of a violent explosion prevented characterisation of the products from a reaction between 2H-pentafluoropropene and triethylammonium azide, but interaction of the latter with perfluorobut-2-yne was shown to yield 3,3,3-trifluoro-1-trifluoromethylprop-1-enyl azide. Pyrolysis of 1H-tetrafluoroprop-1-enyl azide gave αβββ-tetrafluoropropionitrile and 2-fluoro-2-trifluoromethyl-2H-azirine.