Premium
Stable Triazenes Derived from 2‐Alkylaminonaphthalenes and 5‐Nitrobenzo[ c ]‐1,2‐thiazole‐3‐diazonium Hydrogensulfate
Author(s) -
Přikryl Josef,
Macháček Vladimír,
Jansa Petr,
Svobodová Markéta,
Růžička Aleš,
Nachtigall Petr,
Černý Michal
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800180
Subject(s) - chemistry , triazene , thiazole , protonation , nitrogen atom , medicinal chemistry , coupling reaction , diazonium compounds , azo coupling , organic chemistry , polymer chemistry , catalysis , ring (chemistry) , ion
A calculation using the DFT method confirmed that the extraordinary stability of the triazenes formed by an azo coupling reaction of 5‐nitrobenzo[ c ]‐1,2‐thiazole‐3‐diazonium with primary or secondary aromatic amines is caused by the fact that these substances are protonated at the heterocyclic nitrogen atom and not at the nitrogen atom of the triazene grouping –N=N–N(R)Ar. Stable triazenes are also formed by reaction of 5‐nitrobenzo[ c ]‐1,2‐thiazole‐3‐diazonium with 2‐alkylaminonaphthalenes. In the cases of the azo coupling reaction with 2‐methylamino‐ and 2‐ethylaminonaphthalene, the content of triazenes is almost 50 % in the product mixture with the isomeric azo compounds. The structures of the triazenes were confirmed by X‐ray analysis.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)