
%0 Journal Article
%A Johns, SR 
%A Lamberton, JA 
%A Nelson, ER 
%T The reaction of formaldehyde arylhydrazones with excess formaldehyde and the acetylation of arylhydrazines
%J Australian Journal of Chemistry
%D 1973/06/01
%V 26
%N 6
%P 1297-1305
%K 
%R https://doi.org/10.1071/CH9731297
%U https://www.publish.csiro.au/paper/CH9731297 
%X A detailed examination of the reaction of excess formaldehyde with formaldehyde phenylhydrazone and formaldehyde 4-bromophenylhydrazone has shown that the products are the respective 3,6-endo-methylene-1,4- diarylhexahydro-s-tetrazines [(4) and (II)], the symmetrical 2?- oxapropano compounds [(8) and (10)] and the unsymmetrical 2?-oxapropano compounds [(7) and (9)]. These products are analogous to those obtained from formaldehyde 4-nitrophenylhydrazone but are formed in markedly different proportions. Analogous products cannot be obtained from formaldehyde 2,4-dinitro-phenylhydrazone which affords 5-(2,4- dinitrophenylamino)dihydro-1,3,5-dioxazine (12).     A study has also been made of the conditions under which formaldehyde phenyl-hydrazone undergoes oxidative dimerization to glyoxal bisphenylhydrazone, and it has been shown that under appropriate conditions 4-anilino-2-phenyl-2,3,4,5-tetrahydro-1,2,4- triazine (13) can be conveniently prepared.     The acetylation of arylhydrazines has been studied and the products characterized by their N.M.R. spectra. 
