Show simple item record

dc.creatorJakšić, Jovana
dc.creatorMitrović, Aleksandra
dc.creatorTokić-Vujošević, Zorana
dc.creatorMilčić, Miloš
dc.creatorMaslak, Veselin
dc.date.accessioned2021-10-19T09:55:28Z
dc.date.available2021-10-19T09:55:28Z
dc.date.issued2021
dc.identifier.issn2046-2069
dc.identifier.urihttps://farfar.pharmacy.bg.ac.rs/handle/123456789/3982
dc.description.abstractIn this study, b-keto esters as readily available bio-based building blocks were used to decorate the C60 sphere. Generally, cyclopropanated fullerene derivatives are obtained by the standard Bingel–Hirsch procedure. Herein, omitting the iodine from the reaction mixture and adding TEMPO afforded dihydrofuran fused C60 fullerene derivatives. The mechanism of the reaction shifted from nucleophilic aliphatic substitution to oxidative [3 + 2] cycloaddition via fullerenyl cations as an intermediate. This mechanism is proposed based on a series of control experiments with radical scavengers. Therefore, dihydrofuran-fused C60 derivatives were selectively obtained in good yields and their structures were established based on UV-Vis, IR, NMR spectroscopy and mass spectrometry. The electrochemical properties of the synthesized compounds were investigated by cyclic voltammetry. DFT calculations were performed in order to investigate the difference in stability, electronic properties and p-electron delocalization between methano and furano fullerenes.
dc.publisherRoyal Society of Chemistry
dc.relationinfo:eu-repo/grantAgreement/MESTD/inst-2020/200168/RS//
dc.rightsopenAccess
dc.rights.urihttps://creativecommons.org/licenses/by-nc/4.0/
dc.sourceRSC Advances
dc.titleSelective formation of dihydrofuran fused [60] fullerene derivatives by TEMPO mediated [3 + 2] cycloaddition of medium chain β-keto esters to C60
dc.typearticle
dc.rights.licenseBY-NC
dcterms.abstractЈакшић, Јована; Митровић, Aлександра; Маслак, Веселин; Милчић, Милош; Токић-Вујошевић, Зорана;
dc.citation.volume11
dc.citation.issue47
dc.citation.spage29426
dc.citation.epage29432
dc.citation.rankM22
dc.identifier.wos000702237900028
dc.identifier.doi10.1039/d1ra03944j
dc.identifier.scopus2-s2.0-85116237014
dc.identifier.fulltexthttps://farfar.pharmacy.bg.ac.rs/bitstream/id/9254/Selective_formation_of_pub_2021.pdf
dc.type.versionpublishedVersion


Files in this item

Thumbnail

This item appears in the following Collection(s)

Show simple item record