Triazene

Triazenes or Diazoamine are chemical compounds having the general structure R1R2N - N = NR3 in which the name is used for the respective functional group. They should not be confused with the triazines. Triazenes consist of an amino group, which is connected directly to an azo group and therefore also as Diazoaminogruppe ( = triazene ) is called. ( Diazo compounds are compounds in which two nitrogen atoms are bonded directly to each other. ) They can be prepared, for example, by azo coupling of anilines. Triazenes can tautomerize.

Triazenbildung

The Triazenbildung is usually unwanted side reaction in the azo coupling to aromatic amines ( coupling component ). The diazo component is an aromatic amine is diazotized by reaction with nitrous acid.

Which then reacts with the diazonium nucleophilsten point the so-called coupling component, the amine nitrogen in place of the electrophilic substitution of an aryl hydrogen.

Triazenzerfall

The Triazenbildung is reversible. In strong acids decompose on heating these back to their original components, or after tautomerization in others, capable of coupling, compounds ( The former diazo component is formed again as the amine, the former coupling component is now bearing the diazo group ).

Triazenumlagerung

The starting compounds can " migrate " to the desired azo compound. Decomposes the triazene such that it leads to regression of the former Diazokations and the coupling component, obtained in the subsequent azo coupling the desired product. The triazene can (after tautomerization ) but also disintegrate so that the former diazo and coupling the diazotized component forms, the diazo group sitting thus in the 'wrong' molecule. Their decay products are undesirable and only ausbeutevermindernd at best.

Compounds

The simplest compound of this group having the formula NH2N = NH is known as a name even triazene. Another well-known compound of the group is the diphenyl derivative of the triazene, the Diphenyltriazen, also known as diazoaminobenzene (Ph -NH- N = N- Ph). The compounds R1 and R3 are aryl groups often frequently alkyl, allyl or benzyl. By heating in acid solution to triazene compounds into the thermodynamically more stable aminoazo R.sup.1R.sup.2N = NR3 - NH2 can be converted.

Use

Triazenes are used for the preparation of other organic compounds ( for example, resins and drugs such as dacarbazine, diminazene, etc.).