Synthesis of Novel Perhalo 1,3-Heterodienes from N-Bromoperhalo-1-alkanimines

Article abstract of DOI:10.1021/jo00018a010

The hydrolysis of several perhalo-1-bromo-3-aza-3-alkenes (R_xCF=NCF2CF2Br, R_x = CF3, C2F5, ClF2) affords the corresponding acid amide (R_xCONHCF2CF2Br) in excellent yield.Dehydrofluorination of the amides using active KF gives the novel 1,3-heterodienes, perhalo-1-bromo-3-aza-4-oxo-2-alkenes (R_xCON=CFCF2Br) in high yield.Details on the synthesis and properties of the new compounds are given along with some reaction chemistry of the dienes.