Perfluoroalkyl derivatives of nitrogen. Part XXV. The reactions of tristrifluoromethylhydroxylamine and mercuric bistrifluoromethylamide with unsaturated systems

Abstract

Tristrifluoromethylhydroxylamine reacts with perfluorocyclobutene, on irradiation, to give the 1:1 adduct perfluoro-(1-dimethylamino-2-methoxycyclobutane), and lower yields of other products including perfluoro-(1,2-bisdimethylaminocyclobutane), perfluoro-(2,2′-dimethoxybicyclobutyl), and perfluoro-(2-dimethylamino-2′-methoxybicyclobutyl). Reaction with perfluorobut-2-ene is more complex. Perfluoro-2-azapropene gives low yields of the two isomeric 1:1 adducts perfluoro-(2,3-dimethyl-5-oxa-2,3-diazahexane) and perfluoro-(3,5-dimethyl-2-oxa-3,5-diazahexane).

Irradiation of mercuric bistrifluoromethylamide gives perfluorodimethylamine, tetrakistrifluoromethylhydrazine, perfluoro-2-azapropene, and perfluoro-(2,3,5-trimethyl-2,3,5-triazahexane). Photolysis in the presence of perfluorocyclobutene gives perfluoro-(1,2-bisdimethylaminocyclobutane), tetrakistrifluoromethylhydrazine, and smaller amounts of perfluorodimethylamine and perfluoro-2-azapropene.