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

Abstract

A lth o ugh triazenyl alkylolam ines have b ee n re g ard ed as tran sien t m olecular species, exp erim en tal evidence for th e ir stability has b een gradually surfac- E nzym atic dem eth y latio n of l-aryl-3,3-dim ethyltriazen es was recognized as a reversible process and utilized for th e synthesis of th e co rresp o n d in g 3-hydroxym ethyl derivative: 3 -M eth y l-l-p h en y ltriazen e, o b ta in ed from phenylazide by G rig n ard reactio n , readily ad d ed m ethanolic fo rm ald eh y d e to give a sin gle p ro d u ct of low er R f . T he co m p o u n d was id e n tified as 3-hydroxym eth y l-3 -m eth y l-l-p h en y ltriazen e (Fig. 1, A