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- Title
[1,2,5]Selenadiazolo[3,4- b]pyrazines: Synthesis from 3,4-Diamino-1,2,5-selenadiazole and Generation of Persistent Radical Anions.
- Authors
Konstantinova, Lidia S.; Bobkova, Irina E.; Nelyubina, Yulia V.; Chulanova, Elena A.; Irtegova, Irina G.; Vasilieva, Nadezhda V.; Camacho, Paula S.; Ashbrook, Sharon E.; Hua, Guoxiong; Slawin, Alexandra M. Z.; Woollins, J. Derek; Zibarev, Andrey V.; Rakitin, Oleg A.
- Abstract
Previously unknown 3,4-diamino-1,2,5-selenadiazole ( 6) was prepared by hydrolysis of [1,2,5]selenadiazolo[3,4- c][1,2,5]selenadiazole ( 7b) and used in synthesis of novel 1,2,5-selenadiazolo[3,4- b]pyrazines by the Koerner-Hinsberg reaction covering the parent compound 4 and its substituted derivatives 5a- g. The compounds synthesized were characterized by solution and solid-state 77Se NMR, and 6, 5-Ph and 5,6-Me2[1,2,5]selenadiazolo[3,4- b]pyrazines ( 5a, g, respectively) by X-ray diffraction. Electrochemical reduction of 5,6-R2[1,2,5]selenadiazolo[3,4- b]pyrazines 5c, g (R = Ph, Me) into novel persistent radical anions (RAs) was studied by cyclic voltammetry and the RAs [ 5c]- and [ 5g]- were characterized by EPR spectroscopy combined with DFT calculations.
- Subjects
PYRAZINE derivatives; AZOLES; HYDROLYSIS; NUCLEAR magnetic resonance; X-ray diffraction; ELECTRON paramagnetic resonance spectroscopy
- Publication
European Journal of Organic Chemistry, 2015, Vol 2015, Issue 25, p5585
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201500742