Palladium-catalyzed formation of oxazolidinones from biscarbamates: a mechanistic study

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dc.contributor.authorKılbaş, Benan
dc.contributor.authorBalcı, Metin
dc.date.accessioned2020-04-30T23:20:29Z
dc.date.available2020-04-30T23:20:29Z
dc.date.issued2011
dc.departmentDÜ, Fen-Edebiyat Fakültesi, Kimya Bölümüen_US
dc.descriptionWOS: 000287686300001en_US
dc.descriptionPubMed: 21448246en_US
dc.description.abstractOxazolidinones can be synthesized starting from cyclic biscarbamates via a palladium-catalyzed reaction. To test the proposed mechanism of this reaction, first, bicyclonorcarene endoperoxides derived from cyano and carbomethoxy cycloheptatrienes were synthesized and converted into the corresponding diols. The reaction of diols with toluenesulfonyl isocyanate followed by a palladium catalyzed reaction furnished oxazolidinone derivatives in similar yields. It was shown that, if one face of the double bond is blocked by substituents such as H or CN, the reaction also takes place. On the basis of these results, it was assumed that an antiperiplanar orientation of the metal and nucleophile is not necessary to form oxazolidinones. The metal is probably bonded to the allylic system from the same face as the nucleophile.en_US
dc.description.sponsorshipTUBITAK (Scientific and Technological Research Council of Turkey)Turkiye Bilimsel ve Teknolojik Arastirma Kurumu (TUBITAK) [108-M168]; Department of Chemistry at Middle East Technical University; TUBA (Turkish Academy of Sciences)Turkish Academy of Sciencesen_US
dc.description.sponsorshipThe authors are indebted to TUBITAK (Scientific and Technological Research Council of Turkey, (Grant 108-M168), and the Department of Chemistry at Middle East Technical University and TUBA (Turkish Academy of Sciences) for financial support of this work.en_US
dc.identifier.doi10.3762/bjoc.7.33en_US
dc.identifier.endpage253en_US
dc.identifier.issn1860-5397
dc.identifier.scopusqualityQ2en_US
dc.identifier.startpage246en_US
dc.identifier.urihttps://doi.org/10.3762/bjoc.7.33
dc.identifier.urihttps://hdl.handle.net/20.500.12684/4016
dc.identifier.volume7en_US
dc.identifier.wosWOS:000287686300001en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakPubMeden_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherBeilstein-Instituten_US
dc.relation.ispartofBeilstein Journal Of Organic Chemistryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/openAccessen_US
dc.subjectbicyclic endoperoxidesen_US
dc.subjectbiscarbamatesen_US
dc.subjectoxazolidinoneen_US
dc.subjectPd-catalyzed allylic reactionen_US
dc.subjectsinglet oxygenen_US
dc.titlePalladium-catalyzed formation of oxazolidinones from biscarbamates: a mechanistic studyen_US
dc.typeArticleen_US

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