Triazenes

Triazenes are prepared from the N-coupling reaction between diazonium salts and primary or secondary amines.

[5][6] For asymmetrical triazenes, for example (phenyldiazenyl)pyrrolidine (PhN=N−NC4H8), the diazonium salt must be pre-made.

Analogues of Tröger's base containing a symmetric pair of asymmetric triazene side-chains have been obtained similarly.

[8] Triazenes decompose in the presence of protonating or alkylating agents into quaternary amines and diazonium salts; as such triazenes have been used as an in situ source of diazonium that reacted with sodium sulfide to give the corresponding thiophenols.

[5] A strategy for the protection and deprotection of sensitive secondary amines is based on this principle.