Polyfluoroalkyl derivatives of nitrogen. Part XXIX. Reaction of N-bromobistrifluoromethylamine with cis- and trans-but-2-ene and of N-chlorobistrifluoromethylamine with trans-but-2-ene under ionic conditions

Abstract

N-Bromobistrifluoromethylamine reacts with cis- or trans-but-2-ene under ionic conditions (–78° in the dark) to give the stereospecific trans-addition products threo- and erythro-2-bromo-1-methyl-NN-bistrifluoromethyl-propylamine, respectively, in high yield. Reaction of N-chlorobistrifluoromethylamine under comparable conditions with trans-but-2-ene similarly gives the erythro-adduct. Dehydrobromination of the erythro- and threo-N-bromoamine adducts affords cis- and trans-1-methyl-NN-bistrifluoromethylprop-1-enylamine, respectively.