Science of Synthesis

Rück-Braun, K.; Dietrich, S.; Kempa, S.; Priewisch, B., Science of Synthesis, (2007) 31, 1455.

Compounds with two or more diazene units can also be obtained by reacting diazonium ions with coupling components containing further diazene moieties. If the azo group is not connected to the reaction center, substituent effects apply, as discussed for the monocoupling reactions in the previous sections. The arene rings in a diaryldiazene are deactivated by the diazene group. For phenyldiazenes, activation equaling one phenolate group is required; with (monoaminophenyl)diazenes, no bis-diazenes are formed; (monoaminonaphthyl)diazenes, however, react with diazonium ions. Coupling catalysts such as pyridine can be used to counterbalance the deactivating effect of the diazene.

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References

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• 8.Meeeee-Meee, (8888) 88/8, 888.
• 8.Meeeee-Meee, (8888) M 88e8, 88.