ISSN:
0941-1216
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
1,2,3-Triazabutadienes. XXII. Photochemistry of 1-(Carbmethoxy-aryl)- and 1-(Carboxy-aryl)-3-(3-alkyl-benzthiazolinyliden-(2))-triazenes as potential CEL-dyes1-(Carbmethoxy-aryl)-3-(3-alkyl-benzthiazolinyliden-(2))-triazenes (ester-triazenes) (1) were synthesized by coupling of substituted 3-alkyl-2-imino-benzthiazolines-(1,3) with 2-, 3- and 4-carbmethoxy-benzenediazonium salts. The Z-isomers obtained can be transformed into the E-isomers 2 photochemically or by heating. In the presence of acids the E-ester-triazenes are protonated. From the E-ester-triazenes the potassium-salts (4) can be produced by alkaline ester hydrolysis. With hydrochloric acid the E-triazene-potassium salts (4) can be transformed into the protonated (at the N(1)-Atom) E-acid-triazenes (5). Their photochemical properties are identical with those of the protonated E-ester-triazenes (3). The 1-(carboxy-aryl)-3-(3-alkyl-benzthiazolinyliden-(2))-triazenes (E-acid-triazenes) (6) can be obtained from the protonated derivates by deprotonation in the presence of water. The photochemical behaviour of the E-acid-triazenes (6) and of the E-triazene-potassium-salts (4) depends on the position of the carboxy-group (2-position: photolysis, 3- and 4-position: photoisomerization). The uv/vis-spectroscopical and photochemical properties of the triazene-derivates in solution and in polymeric layers are discussed.
Additional Material:
4 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/prac.19923340308
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