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1, 2, 3-Triazabutadiene. XIV. Untersuchungen zur sauren Spaltung Z-E-isomerer 1-Aryl-3-[3-methylbenzthiazolinyliden-(2)]- und 1-Aryl-3-[1,3-dimethylbenzimidazolinyliden-(2)]-triazene

✍ Scribed by Prof. Dr. E. Fanghänel; Dr. J. Hohlfeld

Publisher
John Wiley and Sons
Year
1981
Tongue
English
Weight
466 KB
Volume
323
Category
Article
ISSN
1615-4150

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✦ Synopsis

1,2,3‐Triazabutadienes. XIV. Investigations into the Acidic Cleavage of the Z‐E‐Isomeric 1‐Aryl‐3‐[3‐methylbenzthiazolinyliden‐(2)]‐ and 1‐Aryl‐3‐[1,3‐dimethylbenzimidazolinyliden‐(2)]‐triazenes

The rate of the acid cleavage of the Z‐E‐isomeric 1‐aryl‐3‐[3‐methylbenzthiazolinyliden‐(2)]‐ and 1‐aryl‐3‐[1,3‐dimethyl‐benzimidazolinyliden‐(2)]‐triazenes 1–5 is investigated in dependence on the substituents in the aryl and benzo residue. The Z‐isomeric triazabutadienes are cleft 10^3^ to 10^5^ times faster than the E‐isomers. The ρ‐values are significantly smaller than the ρ‐values of the cleavage of other triazen derivatives. This is explained by an opposite influence of substituents regarding the cleavage of the N^2^‐N^3^‐bond and the equilibrium of protonation of the triazabutadienes. Triazabutadienes with a pronounced polymethine like structure decompose more rapidly than is conformable to their σ‐values. For the E‐isomers a V‐shape of the Hammett‐correlation is found. The considerable differences in the rate of heterolysis of the Z‐E‐isomers can be used for a negatively working diazo material which is sensitive to visible light.

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