Perfluoroalkyl derivatives of nitrogen. Part XXI. Some reactions of bistrifluoromethylnitroxide
Abstract
Bistrifluoromethylnitroxide combines readily with ethylene, tetrafluoroethylene, hexafluoropropene, or hexafluorocyclobutene to give almost quantitative yields of the compounds 1,2-bis(NN-bistrifluoromethylnitroxy)-ethane, perfluoro-[1,2-bis(NN-dimethylnitroxy)ethane], perfluoro-[1,2-bis(NN-dimethylnitroxy)propane], and perfluoro-[1,2-bis(NN-dimethylnitroxy)cyclobutane], severally. It reacts with trifluoronitrosomethane to form perfluoro-(2,4-dimethyl-3-oxa-2,4-diazapentane), and with trifluoroiodomethane to yield tristrifluoromethylhydroxylamine. Catalytic reduction of bistrifluoromethylnitroxide affords bistrifluoromethylhydroxylamine, and hot iron converts it into perfluoro(methylenemethylamine). Bistrifluoromethylnitroxide and toluene interact readily to yield O-benzyl-NN-bistrifluoromethylhydroxylamine and bistrifluoromethylhydroxylamine.