Triazenes are organic compounds that contain the functional group R1−N=N−NR2R3, where the R are each any of various types of substituent groups. [2] Some anti-cancer medications and dyes are triazenes. [3] Formally, the triazenes are related to the unstable chemical triazene, H2N−N=NH.
Triazenes are prepared from the N-coupling reaction between diazonium salts and primary or secondary amines. [4] The coupling reactions are typically mild, using a base such as sodium acetate, [5] sodium carbonate, [5] or sodium bicarbonate. [4]
The diazonium reagents are themselves available starting from amines. For symmetrical triazenes derived from primary amines, partial diazotization gives a mixture of the original amine and its diazo derivative that then couple with each other. For example, 1,3-diphenyltriazene (PhN=N−NHPh) can be made from aniline in a one-pot reaction. [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. [7]
Triazenes derived from primary amines engage in tautomerism. In the case of symmetric triazenes, the tautomers are identical.
Triazenes can be converted to diazonium salts. [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. [9]
Polymeric triazenes are applied as conductive and absorbent materials. [10] Triazenes have been used in the synthesis of cinnoline, functionalized lactams, and coumarins. [9] [8]
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Triazenes are organic compounds that contain the functional group R1−N=N−NR2R3, where the R are each any of various types of substituent groups. [2] Some anti-cancer medications and dyes are triazenes. [3] Formally, the triazenes are related to the unstable chemical triazene, H2N−N=NH.
Triazenes are prepared from the N-coupling reaction between diazonium salts and primary or secondary amines. [4] The coupling reactions are typically mild, using a base such as sodium acetate, [5] sodium carbonate, [5] or sodium bicarbonate. [4]
The diazonium reagents are themselves available starting from amines. For symmetrical triazenes derived from primary amines, partial diazotization gives a mixture of the original amine and its diazo derivative that then couple with each other. For example, 1,3-diphenyltriazene (PhN=N−NHPh) can be made from aniline in a one-pot reaction. [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. [7]
Triazenes derived from primary amines engage in tautomerism. In the case of symmetric triazenes, the tautomers are identical.
Triazenes can be converted to diazonium salts. [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. [9]
Polymeric triazenes are applied as conductive and absorbent materials. [10] Triazenes have been used in the synthesis of cinnoline, functionalized lactams, and coumarins. [9] [8]
{{
cite journal}}
: CS1 maint: multiple names: authors list (
link)