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General structure of a triazene

Triazene is the chemical compound NH2N=NH but it has also given name to the functional group consisting of an amine directly bonding to an azo group, i.e. with the linkage R2N-N=NR' where R and R' are substituents. The functional group is also called a diazoamino group (but only one of the two substituents R and R' may be hydrogen) because it is related to a diazo group.

A well known example is of a triazene is diphenyl derivative,[1] PhNH-N=NPh (m.p. 100 °C, CAS #136-35-6). It is prepared from phenyldiazonium salts and aniline in the presence of base:

PhN2+ + PhNH2 → PhNHN=NPh + H+

References

  1. ^ Hartman, W. W.; Dickey, J. B. "Diazoaminobenzene" Organic Syntheses, Collected Volume 2, p.163 (1943). http://www.orgsyn.org/orgsyn/pdfs/CV2P0163.pdf

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