Polyfluoroalkyl derivatives of nitrogen. Part XXX. Reaction of N-chlorobistrifluoromethylamine with propene and vinyl fluoride and of N-iodobistrifluoromethylamine with vinyl fluoride under ionic conditions

Abstract

Reaction of N-chlorobistrifluoromethylamine with propene under conditions presumed to involve ionic intermediates (–24° in the dark) gives a mixture of 2-chloro-1-methyl-NN-bistrifluoromethylethylamine and 2-chloro-NN-bistrifluoromethylpropylamine in the ratio 60 : 40. Vinyl fluoride reacts with the N-iodoamine under identical conditions to give mainly 1-fluoro-2-iodo-NN-bistrifluoromethylethylamine together with small amounts of 2-fluoro-2-iodo-NN-bistrifluoromethylethylamine, 1,1-difluoro-2-iodoethane, and perfluoro-2-azapropene. In contrast the N-chloro-amine does not react with vinyl fluoride at –24°, but at room temperature in the dark the 1 : 1 adducts 2-chloro-2-fluoro- and 2-chloro-1-fluoro-NN-bistrifluoromethylethylamine are formed in the ratio 93:7 by a free-radical reaction.