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Electrochemical synthesis of heterocyclic compounds. Part 6. The redox behaviour of the formazan–tetrazolium salt system in acetonitrile

1979; Royal Society of Chemistry; Issue: 2 Linguagem: Inglês

10.1039/p29790000166

2050-8239

Ibro Tabaković, M. Trkovnik, Z. GRUJIC,

bioluminescence and chemiluminescence research

The synthesis in quantitative yield of 2,3,5-triaryltetrazolium salts by anodic oxidation of formazans is described. The redox behaviour of the 1,3,5-triphenylformazan–2,3,5-triphenyltetrazolium perchlorate system was studied in detail using electroanalytical techniques. It is concluded that two-electron oxidative cyclisation of formazan to tetrazolium salt occurs through an e-c-P-e-(d) mechanism, using the nomenclature of Andrieux and Savéant. The reduction of the tetrazolium salt to the formazan goes by opposite mechanistic pathways (e-P-c-e) to those for the electrochemical oxidation of formazan.