Structural elucidation of dioxa‐cage compounds from tetrahydroisobenzofuran‐1(3H)‐one: analysis of NMR data and GIAO chemical shifts calculations

dc.creatorResende, Gabriela da Costa
dc.creatorAlvarenga, Elson Santiago
dc.date2018-04-19T12:16:44Z
dc.date2018-04-19T12:16:44Z
dc.date2016-08-02
dc.date.accessioned2023-09-27T22:09:54Z
dc.date.available2023-09-27T22:09:54Z
dc.identifier1097458X
dc.identifierhttps://doi.org/10.1002/mrc.4483
dc.identifierhttp://www.locus.ufv.br/handle/123456789/18824
dc.identifier.urihttps://repositorioslatinoamericanos.uchile.cl/handle/2250/8971568
dc.descriptionThe polycyclic compounds, especially the dioxa-cages, have attracted considerable attention in recent years. In our work, a series of 9β-substituted 3-oxo-4,11-dioxatetracyclo[5.2.1.1 5,8 .0 2,6 ]undecane compounds were unexpectedly isolated during bromination, chlorination and epoxidation reactions of the 3-hydroxy-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1(3H)-one. After careful analysis of the NMR data, the chemical shifts of the isolated and the expected products were predicted by theoretical calculations using density functional theory and gauge including atomic orbitals. The best correlation between calculated and experimental data was evaluated by comparing mean absolute errors and applying DP4 probability methodology. Results from both approaches indicated a correct structural elucidation.
dc.formatpdf
dc.formatapplication/pdf
dc.languageeng
dc.publisherMedical Research Council
dc.relationv. 54, Issue 12, p. 968-974, December 2016
dc.rightsJohn Wiley & Sons, Ltd.
dc.subjectNMR
dc.subject1H
dc.subject13C
dc.subjectNMR calculations
dc.subjectDFT-GIAO
dc.subjectNorbornene derivatives
dc.subjectDioxa-cage compounds
dc.subjectElectrophilic addition
dc.titleStructural elucidation of dioxa‐cage compounds from tetrahydroisobenzofuran‐1(3H)‐one: analysis of NMR data and GIAO chemical shifts calculations
dc.typeArtigo


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