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1,2,5-Selenadiazolo[3,4-b]pyrazines : synthesis from 3,4-Diamino-1,2,5-selenadiazole and Generation of Persistent Radical Anions

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dc.contributor.authorKonstantinova, Lidia S.
dc.contributor.authorBobkova, Irina E.
dc.contributor.authorNelyubina, Yulia V.
dc.contributor.authorChulanova, Elena A.
dc.contributor.authorIrtegova, Irina G.
dc.contributor.authorVasilieva, Nadezhda V.
dc.contributor.authorSanz Camacho, Paula
dc.contributor.authorAshbrook, Sharon Elizabeth
dc.contributor.authorHua, Guoxiong
dc.contributor.authorSlawin, Alexandra Martha Zoya
dc.contributor.authorWoollins, J Derek
dc.contributor.authorZibarev, Andrey V.
dc.contributor.authorRakitin, Oleg A.
dc.date.accessioned2016-07-22T23:30:58Z
dc.date.available2016-07-22T23:30:58Z
dc.date.issued2015-09
dc.identifier.citationKonstantinova , L S , Bobkova , I E , Nelyubina , Y V , Chulanova , E A , Irtegova , I G , Vasilieva , N V , Sanz Camacho , P , Ashbrook , S E , Hua , G , Slawin , A M Z , Woollins , J D , Zibarev , A V & Rakitin , O A 2015 , ' 1,2,5-Selenadiazolo[3,4-b]pyrazines : synthesis from 3,4-Diamino-1,2,5-selenadiazole and Generation of Persistent Radical Anions ' , European Journal of Organic Chemistry , vol. 2015 , no. 25 , pp. 5585-5593 . https://doi.org/10.1002/ejoc.201500742en
dc.identifier.issn1434-193X
dc.identifier.otherPURE: 200610552
dc.identifier.otherPURE UUID: 43566c54-c4c9-4dcf-b7ba-110c3f67fc45
dc.identifier.otherScopus: 84939653854
dc.identifier.otherORCID: /0000-0002-4538-6782/work/56638971
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861804
dc.identifier.otherORCID: /0000-0002-1498-9652/work/31779173
dc.identifier.otherWOS: 000360064500012
dc.identifier.urihttps://hdl.handle.net/10023/9198
dc.descriptionThe authors acknowledge financial support from the Russian Foundation for Basic Research (Project 13-03-00072), the Presidium of the Russian Academy of Sciences (Programme No.8, Project 8.14) and the Leverhulme Trust (Project IN-2012-094). I.G.I, N.V.V., E.A.C. and A.V.Z. are grateful to the Ministry of Education and Science of the Russian Federation (Project of Joint Laboratories of Siberian Branch of the Russian Academy of Sciences and National Research Universities), and E.A.C. to the BP Company for postgraduate scholarship.en
dc.description.abstractSynthesis of 3,4-disubstituted and fused 1,2,5-selenadiazolo[3,4-b]pyrazines via previously unknown 3,4-diamino-1,2,5-selenadiazole has been achieved in moderate to high yields. The compounds synthesized were characterized by elemental analysis, MS and multinuclear (1H, 13C and 77Se) NMR, and the structures of 3,4-diamino-1,2,5-selenadiazole, 5,6-dimethyl[1,2,5]selenadiazolo[3,4-b]pyrazine and 5-phenyl[1,2,5]selenadiazolo[3,4-b]pyrazine were confirmed by X-ray diffraction. Electrochemical reduction of 5,6-R2-1,2,5-selenadiazolo[3,4-b]pyrazines (R = Me, Ph) into persistent radical anions (RAs) was studied by cyclic voltammetry and the RAs were characterized by EPR spectroscopy combined with DFT calculations
dc.format.extent9
dc.language.isoeng
dc.relation.ispartofEuropean Journal of Organic Chemistryen
dc.rightsCopyright © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the accepted version of the following article: Konstantinova, L. S., Bobkova, I. E., Nelyubina, Y. V., Chulanova, E. A., Irtegova, I. G., Vasilieva, N. V., Camacho, P. S., Ashbrook, S. E., Hua, G., Slawin, A. M. Z., Woollins, J. D., Zibarev, A. V. and Rakitin, O. A. (2015), [1,2,5]Selenadiazolo[3,4-b]pyrazines: Synthesis from 3,4-Diamino-1,2,5-selena­diazole and Generation of Persistent Radical Anions. Eur. J. Org. Chem., which has been published in final form at http://dx.doi.org/10.1002/ejoc.201500742en
dc.rightsCopyright © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the accepted version of the following article: Konstantinova, L. S., Bobkova, I. E., Nelyubina, Y. V., Chulanova, E. A., Irtegova, I. G., Vasilieva, N. V., Camacho, P. S., Ashbrook, S. E., Hua, G., Slawin, A. M. Z., Woollins, J. D., Zibarev, A. V. and Rakitin, O. A. (2015), [1,2,5]Selenadiazolo[3,4-b]pyrazines: Synthesis from 3,4-Diamino-1,2,5-selena­diazole and Generation of Persistent Radical Anions. Eur. J. Org. Chem., which has been published in final form at http://dx.doi.org/10.1002/ejoc.201500742en
dc.subjectSynthesisen
dc.subject[1,2,5]selenadiazolo[3,4-b]pyrazinesen
dc.subjectα- diketonesen
dc.subject3,4-diamino-1,2,5-selenadiazoleen
dc.subjectCyclic voltammetryen
dc.subjectEPR spectroscopyen
dc.subjectDFT calculationsen
dc.subjectX-ray diffractionen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.title1,2,5-Selenadiazolo[3,4-b]pyrazines : synthesis from 3,4-Diamino-1,2,5-selenadiazole and Generation of Persistent Radical Anionsen
dc.typeJournal articleen
dc.contributor.sponsorThe Leverhulme Trusten
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorEPSRCen
dc.contributor.sponsorEPSRCen
dc.description.versionPostprinten
dc.description.versionPostprinten
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews. Office of the Principalen
dc.identifier.doihttps://doi.org/10.1002/ejoc.201500742
dc.description.statusPeer revieweden
dc.date.embargoedUntil2016-07-23
dc.identifier.urlhttp://onlinelibrary.wiley.com/doi/10.1002/ejoc.201500742/suppinfoen
dc.identifier.grantnumberIN-2012-094en
dc.identifier.grantnumberEP/K503940/1en
dc.identifier.grantnumberEP/K031252/1en
dc.identifier.grantnumberEP/K039210/1en


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