Polyfluoroalkyl derivatives of nitrogen. Part XXXVIII. Reaction of N-bromobistrifluoromethylamine with allyl chloride; preparation of NN-bistrifluoromethylprop-2-enylamine

Abstract

Reaction of N-bromobistrifluoromethylamine with allyl chloride at –78° in the dark gives the 1 : 1 adducts 2-bromo-3-chloro-NN-bistrifluoromethylpropylamine and 1 -bromomethyl-2-chloro-NN-bistrifluoromethylethylamine in the ratio 66 : 34; at room temperature in the vapour phase in light the same adducts are formed in the ratio 90 : 10. Dehydrohalogenation of the former adduct gives mainly cis- and trans-3-chloro-NN-bistrifluoromethylprop-1 -enylamine and 2-bromo-NN-bistrifluoromethylprop-2-enylamine, together with a small amount of NN-bistri-fluoromethylpropadienylamine; the latter adduct affords a mixture of 3-chloro- and 3-bromo-2-(NN-bistrifluoro-methylamino)propene with the former olefin predominating. Dehalogenation of the 2-bromo-3-chloro-compound gives NN-bistrifluoromethylprop-2-enylamine in good yield.