Studies in azide chemistry. Part I. Synthesis of perfluoropropenyl azide and its conversion into perfluoro-(2- and 3-methyl-2H-azirine)

Abstract

Perfluoropropene reacts with triethylammonium azide in sym-tetrachloroethane or sodium azide in dimethylformamide at low temperatures to give perfluoropropenyl azide, which decomposes at 20° into nitrogen and perfluoro-(2-methyl-2H-azirine). Hydrolysis of the azirine provides trifluoropyruvic acid. Isomerisation of perfluoro-(2-methyl-2H-azirine) to perfluoro-(3-methyl-2H-azirine) occurs when it is treated with anhydrous hydrogen fluoride, a procedure that also leads to the formation of perfluoro-(2-methylaziridine).