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Modulation of the N-azo coupling betw een ring-substituted arenediazonium chlorides and premixed m ethylam ine-form aldehyde leads not only to 1-aryl-3-hydroxymethyl-3-methyltriazenes and their dimers, but also to unexpected cyclic and com plex products. The syntheses comprise reactions with arenediazonium chlorides bearing both - M and + M substituents at para and ortho/para positions of the phenyl ring. One of the major constituents isolated from a mixture of products is the O-acetate ot 3-hydroxymethyl-3-methyl-1-(2,4,6&gt;-trichlorophenyl)triazene. This product was obtained from the reaction of 2,4,6-trichlorobenzenediazonium chloride and methylamine- formaldehyde mixture which was then stabilized by acetylation.

zeitschrift für naturforschung c

Reactions of Substituted Arenediazonium Chlorides with Methylamine- Formaldehyde Premix Revisited: Reactivity and Transformations of Methylolamine Intermediates and Their Biological Significance