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Electrochemistry of triazenes—Part 4. Reaction of diazonium ions generated electrochemically from 1-aryl-3,3-dimethyltriazenes in acetonitrile

✍ Scribed by Xudong Wei; Bernd speiser

Publisher
Elsevier Science
Year
1995
Tongue
English
Weight
669 KB
Volume
40
Category
Article
ISSN
0013-4686

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✦ Synopsis

Several l-(p-R-aryl)-3,3dimethyltriazenes are anodically oxidized at a Pt electrode in acetonitrile/O.l M tetrabutylammonium hexafluorophosphate in preparative-scale controlled potential bulk electrolyses. The overall oxidation process produces diazonium ions by cleavage of the N(2)-N(3) bond in the respective primary products, the triazene radical cations, and a subsequent second electron transfer. The diazonium ions react with cathodically formed diacetonitrile (3-aminocrotononitrile) in a paired-type electrolysis to form enamines, which undergo hydrolysis to a-arylhydrazono-ketonitriles or an oxidative ring formation to give triazoles. This reaction sequence opens the way to a simple one-pot electrochemical synthesis of these heterocycles from triazenes. Only for R = NO, a parallel reaction forming nitrobenzene via a diazenyl radical is found.

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