Synthesis, reactions and DFT study of tropolone N,N-dimethylthiocarbamate

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dc.authoridZaim, Omer/0000-0002-3472-5611
dc.authoridAviyente, Viktorya/0000-0001-9430-4096
dc.authoridTuzun, Nurcan/0000-0001-5225-3876
dc.authoridOzcan, hafize/0000-0002-8031-6755
dc.authorwosidZaim, Omer/Q-7770-2019
dc.authorwosidZaim, Ömer/AAI-1470-2021
dc.authorwosidAviyente, Viktorya/Q-2759-2015
dc.authorwosidTuzun, Nurcan/N-9217-2013
dc.authorwosidOzcan, hafize/KJM-5364-2024
dc.contributor.authorZaim, Omer
dc.contributor.authorTuzun, Nurcan S.
dc.contributor.authorCevik, Busra
dc.contributor.authorOzcan, Hafize
dc.contributor.authorBoz, Esra
dc.date.accessioned2024-06-12T11:16:43Z
dc.date.available2024-06-12T11:16:43Z
dc.date.issued2015
dc.departmentTrakya Üniversitesien_US
dc.description.abstractA new tropolone derivative namely O-(7-oxocyclohepta-1,3,5-trienyl) dimethylthiocarbamate was synthesized from tropolone and N,N-dimethylthiocarbamoyl chloride and its reactions with lithium halides in acidic media were examined. The product of each lithium halide treatment was identical and identified as S-(3-oxocyclohepta-1,4,6-trienyl) dimethylcarbamothioate. Eventually it was converted to 3-mercapto 2,4,6-cycloheptatrien-1-one on treatment with base. DFT calculations at the B3LYP/6-311++G** level were performed on the key elimination step of the mechanism, which was proposed by Ponaras et al. on analogous five-membered ring systems. The experimentally observed regioselectivity was correlated to the calculated activation barriers on five and seven-membered systems in the elimination step such that in both cases, experimentally observed product was favored over the alternative one. Thus, quantum mechanical calculations have provided insights into the synthetic pathway and regioselectivity of the reaction in this study, in comparison to the analogous five-membered system. (C) 2015 Elsevier Ltd. All rights reserved.en_US
dc.description.sponsorshipscientific research project commission of Trakya University (TUBAP) [TUBAP 2013/68]; ITU BAP Project [3087]; National High Performance Computing Center at ITU [10732009]en_US
dc.description.sponsorshipWe gratefully acknowledge the financial support of scientific research project commission of Trakya University (TUBAP 2013/68) and the ITU BAP Project (Grant No: 3087). Computational sources were provided by the National High Performance Computing Center at ITU (Grant No: 10732009).en_US
dc.identifier.doi10.1016/j.tet.2015.05.100
dc.identifier.endpage5398en_US
dc.identifier.issn0040-4020
dc.identifier.issn1464-5416
dc.identifier.issue33en_US
dc.identifier.scopus2-s2.0-84936890046en_US
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage5391en_US
dc.identifier.urihttps://doi.org/10.1016/j.tet.2015.05.100
dc.identifier.urihttps://hdl.handle.net/20.500.14551/24421
dc.identifier.volume71en_US
dc.identifier.wosWOS:000358394100022en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherPergamon-Elsevier Science Ltden_US
dc.relation.ispartofTetrahedronen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subjectTropoloneen_US
dc.subjectThiocarbamateen_US
dc.subjectThioleen_US
dc.subjectDimethylthiocarbamoyl Chlorideen_US
dc.subjectDFTen_US
dc.subjectB3LYPen_US
dc.subjectReplacementen_US
dc.subjectDiosphenolsen_US
dc.subjectElaborationen_US
dc.titleSynthesis, reactions and DFT study of tropolone N,N-dimethylthiocarbamateen_US
dc.typeArticleen_US

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