Electrophilic Substitution Reaction at Azomethine Carbon Atom. Acylation of Aliphatic Aldehyde Hydrazones

Article abstract of DOI:10.1021/jo00238a009

Formaldehyde dialkylhydrazones were found to undergo an electrophilic substitution reaction very easily at the azomethine carbon atom when treated with trifluoroacetic anhydride.Bistrifluoroacetylation is also possible.As an interesting extension of this reaction, trifluoroacetylation of dialkylhydrazones of aliphatic aldehydes and α,β-unsaturated aldehydes, was achieved.Similar reactions of these hydrazones with some other acylating reagents were also studied.