The reaction of formaldehyde arylhydrazones with acetic anhydride

Abstract

Formaldehyde 2,4-dinitrophenylhydrazone does not react with acetic anhydride, whereas formaldehyde 4-nitrophenylhydrazone affords a complex mixture of products from which formaldehyde N,-acetyl-4-nitrophenylhydrazone, N_β-acetyl-4-nitrophenylhydrazine, N_α,N_β-diacetyl-4-nitrophenylhydrazine and 1,4-di(4'-nitrophenyl)-2,5-endo-methanohexahydro-s-tetrazine have been isolated.Formaldehyde phenylhydrazone reacts with acetic anhydride under mild conditions to give N_α,N_β diacetylphenylhydrazine,1,4-diphenylhexahydro-2,5-endo-methano-s-tetrazine, 2,5-diacetyl-1,4-diphenylhexahydro-s-tetrazine and two other products C₁₇H₂₀N₄O₂ and C₃₂H₃₆N₈O₂ which areconsidered to be (7) and (15) respectively.