1,3-Diphenyltriazene Explained

1,3-Diphenyltriazene is the organic compound with the formula PhN=N-N(H)Ph (Ph = C₆H₅). It is a prototypical triazene, i.e. a compound with the functional group RN=N-NR₂. It is a pale yellow solid, prepared by the reaction of phenyldiazonium salts with aniline.^[1] In practise, phenyldiazonium salts are also prepared from alanine, thus 1,3-diphenyltriazene can be prepared from analine in one-pot reaction via partial diazotization.^{[2] [3]} It is a planar molecule. The N-N distances are 1.287 and 1.337 Å.^[4]

Notes and References

1. Hartman . W. W. . Dickey . J. B.. Diazoaminobenzene . Organic Syntheses . 14 . 24 . 1934 . 10.15227/orgsyn.014.0024.
2. Kazem-Rostami. M.. Khazaei. A.. Moosavi-Zare. A. R.. Bayat. M.. Saednia. S.. 2012. Novel One-Pot Synthesis of Thiophenols from Related Triazenes under Mild Conditions. Synlett. 23. 13. 1893–1896. 10.1055/s-0032-1316557. 196805424 .
3. Hartman, W. W.; Dickey, J. B.. 1934. Diazoaminobenzene. Organic Syntheses. 14. 24. 10.15227/orgsyn.014.0024.
4. 10.1002/zaac.201100227. Reaktionen von 1,3-Diphenyltriazenid mit Cu⁺ und Tl⁺. Zeitschrift für anorganische und allgemeine Chemie. 637. 1784–1789. 2011. Lego. Christian. Neumüller. Bernhard. 12.