1,2,2-Trichlorovinylamines trichloroacetamides

Speziale and his co-workers have carried out comprehensive studies of the reactions of phosphorus compounds. It has been shown 108) that the reaction of N,N-dialkyl-a-trichloroacetamides (127) with phosphites and phosphines gives trichlorovinylamines (128). In general the trialkyl-phosphines gave somewhat higher yields (60 to 83%) and purer products... 

Reaction of 7V,A-diethyl-2,2,2-trichloroacetamide with trialkyl phosphites or triphenylphosphine to give N, N-diethyl-1,2,2-trichlorovinylamine [152-154],... 

N,N-Diethyl-l,2,2-trichlorovinylamine has been prepared by the action of trimethyl, triethyl, or triisopropyl phosphite or triphenylphosphine on N,N-diethyl-2,2,2-trichloroacetamide., These methods require a reaction temperature of 150-160° and several distillations in order to obtain a pure product. Consequently, the yields of the vinylamine are lower than by the present procedure.3... 

The procedure has also been applied to the synthesis of N,N-dimethyl-l,2,2-trichlorovinylamine from trichloroacetamide (60% yield),3 and it probably is a general means of preparing N,N-dialkyl-l,2,2-trichlorovinylamines. The reaction is an unusual one involving reduction of the amide and halogen migration and is of theoretical interest. 

The reaction of trichlorovinylamines, such as LXXXII, which are obtained from N,N-disubstituted 2.2,2-trichloroacetamides and tertiary phosphines, with hydrogen chloride affords the iminium salts LXXXIII... 

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