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Ferrier rearrangement promoted by an electrochemically generated zirconium catalyst
dc.creator | Stevanović, Dragana D. | |
dc.creator | Pejović, Anka | |
dc.creator | Damljanović, Ivan S. | |
dc.creator | Minić, Aleksandra | |
dc.creator | Bogdanović, Goran A. | |
dc.creator | Vukićević, Mirjana | |
dc.creator | Radulović, Niko S. | |
dc.creator | Vukićević, Rastko D. | |
dc.date.accessioned | 2018-03-01T16:03:04Z | |
dc.date.available | 2018-03-01T16:03:04Z | |
dc.date.issued | 2015 | |
dc.identifier.issn | 0008-6215 | |
dc.identifier.issn | 1873-426X | |
dc.identifier.uri | https://vinar.vin.bg.ac.rs/handle/123456789/489 | |
dc.description.abstract | In situ generated zirconium catalyst from a sacrificial zirconium anode was successfully applied to promote Ferrier rearrangement of 3,4,5-tri-O-acetyl-D-glucal and 6-deoxy-3,4-di-O-acetyl-L-glucal (3,4-di- O-acetyl-L-rhamnal) in the presence of three thiols and eleven thiophenols as nucleophiles. A simple constant current electrolysis (20 mA, 0.4 F mol(-1)) of an acetonitrile solution of lithium perchlorate (0.1 M) containing the corresponding glycal and S-nucleophiles, using a zirconium anode and a platinum cathode resulted in the successful synthesis of the corresponding 2,3-unsaturated peracetylated thioglycosides (with an average anomer ratio alpha/beta-4.129 in the case of peracetylated D-glucal and 8.740 in the case of L-rhamnal). The same procedure proved to be appropriate in synthesizing dihydropyran derivatives (C-glycosides) using allyltrimethylsilane as the nucleophile (only alpha-anomers were obtained). All new compounds were fully characterized by spectral data, whereas single-crystal X-ray analysis was performed for two thioglycosides. (C) 2015 Elsevier Ltd. All rights reserved. | en |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172034/RS// | |
dc.rights | restrictedAccess | en |
dc.source | Carbohydrate Research | en |
dc.subject | Peracetylated D-glucal | en |
dc.subject | Peracetylated L-rhamnal | en |
dc.subject | Thiophenols | en |
dc.subject | Pseudoglycals | en |
dc.subject | Anodic generation of catalyst | en |
dc.subject | Zirconium | en |
dc.title | Ferrier rearrangement promoted by an electrochemically generated zirconium catalyst | en |
dc.type | article | en |
dcterms.abstract | Дамљановиц, Иван; Богдановић Горан; Радуловиц, Нико С.; Вукицевиц, Растко Д.; Миниц, Aлександра; Стевановиц, Драгана; Вукицевиц, Мирјана; Пејовиц, Aнка; | |
dc.citation.volume | 407 | |
dc.citation.spage | 111 | |
dc.citation.epage | 121 | |
dc.identifier.wos | 000352217900016 | |
dc.identifier.doi | 10.1016/j.carres.2015.02.001 | |
dc.citation.rank | M22 | |
dc.identifier.pmid | 25746956 | |
dc.type.version | publishedVersion | |
dc.identifier.scopus | 2-s2.0-84923858552 |
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