Hydroxylamines hydroxytriazenes

The reaction of arenediazonium ions with hydroxylamine is known, but has been little investigated (Gattermann and Ebert, 1916). The l-aryl-3-hydroxytriazene (6.23) formed initially is in most cases unstable (except if Ar = anthraquinonyl). Under alkaline conditions elimination of N20 yields the amine, whereas the aryl azide is formed in the presence of acid (Scheme 6-15). There are, however, better methods for the synthesis of aryl azides (review Biffin et al., 1971, p. 147). 

Many of the 3-hydroxytriazene derivatives produced by diazo-coupling onto N-alkyl or A-aryl hydroxylamines decompose explosively above their m.p.s. However, the heavy metal derivatives are stable and used in analytical chemistry. 

C. Some Other Related Species that will be Ignored Hydroxylamines, Nitrosohydroxylamines, Hydroxytriazenes... 

Having chosen to ignore amidoximes with the general formula R C(NR R )=N—OH legitimizes our decision to ignore in this chapter A-hydroxytriazenes with their functionality R N(OH)—N=N—R (or are they the tautomeric triazene A-oxides, R N(0)= N—NH—R ) because they are all A-substituted hydroxylamines. 

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See also in sourсe #XX -- [ , ]

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