Polyfluoroalkyl derivatives of nitrogen. Part XXXVI. Photochemical reaction of N-bromo- and N-chloro-bistrifluoromethylamine with cis- or trans-but-2-ene, and the synthesis of 1,2-di(bistrifluoromethylamino)- difluoroethylene and 2-bromo-1,2-difluoro-NN-bistrifluoromethylvinylamine

Abstract

Photochemical reactions of N-bromobistrifluoromethylamine with cis- or trans-but-2-ene gives the 1:1 adducts erythro- and threo-2-bromo-1-methyl-NN-bistrifluoromethylpropylamine in the ratios 17:83 and 77:23, respectively. The corresponding N-chloro-amine reactions afford the erythro- and threo- 1:1 adducts in the ratios 10:90 and 87:13, respectively. A thermal reaction of the N-bromo-amine with 1,2-difluoro-NN-bistrifluoromethylvinylamine gives 1,2-di(bistrifluoromethylamino)-2-bromo-1,2-difluoroethane in high yield, which is dehydrobrominated to give 1,2-di(bistrifluoromethylamino)difluoroethylene. The synthesis of cis- and trans-2-bromo-1,2-difluoro-NN-bistrifluoromethylvinylamine is described.