
%0 Journal Article
%A Lamberton, JA 
%A Nelson, ER 
%T The reaction of formaldehyde with mixtures of arylhydrazines and amines
%J Australian Journal of Chemistry
%D 1976/08/01
%V 29
%N 8
%P 1853-1857
%K 
%R https://doi.org/10.1071/CH9761853
%U https://www.publish.csiro.au/paper/CH9761853 
%X Phenylhydrazine, aniline and formaldehyde react under appropriate conditions to give a high yield of phenyl(phenylazoethyl)amine (1). Under analogous conditions N-methyl-N-phenylhydrazine, N-methylaniline and formaldehyde give 2-(N-methy1anilino)acetaldehyde methylphenylhydrazone (2). With morpholine and phenylhydrazine formaldehyde gives a product C24H34N6O2 considered from spectroscopic evidence to be 2,5-di(morpholinomethyl)-1,4-diphenylhexahydro-s-tetrazine (4) derived from an N-Mannich reaction between morpholine and 1,4-diphenylhexahydro-s-tetrazine.A change in the relative proportions of phenylhydrazine, aniline and formaldehyde results in the formation of a further compound C44H46N10 considered from spectroscopic data to be 2,5-di[Nphenyl-N-(phenylazoethyl)aminomethyl]-l,4-diphenylhexahyo-s-tetrazine (7) derived from an N-Mannich reaction between phenyl(phenylazoethyl)amine (1) and 1,4-diphenylhexahydro-stetrazine. 
