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On the strong difference in reactivity of acyclic and cyclic diazodiketones with thioketones: experimental results and quantum-chemical interpretation

dc.contributor.authorMereshchenko, Andrey S.
dc.contributor.authorAlexey, V. Ivanov
dc.contributor.authorBaranovskii, Viktor I.
dc.contributor.authorRodina, Ludmila L.
dc.contributor.authorNikolaev, Valerij A.
dc.contributor.authorMloston, Grzegorz
dc.date.accessioned2015-08-27T15:12:33Z
dc.date.available2015-08-27T15:12:33Z
dc.date.issued2015-04-20
dc.identifier.issn1860-5397
dc.identifier.urihttp://hdl.handle.net/11089/11580
dc.description.abstractThe 1,3-dipolar cycloaddition of acyclic 2-diazo-1,3-dicarbonyl compounds (DDC) and thioketones preferably occurs with Z,Econformers and leads to the formation of transient thiocarbonyl ylides in two stages. The thermodynamically favorable further transformation of C=S ylides bearing at least one acyl group is identified as the 1,5-electrocyclization into 1,3-oxathioles. However, in the case of diazomalonates, the dominating process is 1,3-cyclization into thiiranes followed by their spontaneous desulfurization yielding the corresponding alkenes. Finally, carbocyclic diazodiketones are much less reactive under similar conditions due to the locked cyclic structure and are unfavorable for the 1,3-dipolar cycloaddition due to the Z,Z-conformation of the diazo molecule. This structure results in high, positive values of the Gibbs free energy change for the first stage of the cycloaddition process.pl_PL
dc.description.sponsorshipA. V. I. thanks the Saint Petersburg State University for financial support of his stay at the University of Łódź with Prof. G. Mloston (order 1831/1; 02.06.2011). A. S. M. acknowledges the Saint Petersburg State University for financial support in the form of a postdoctoral fellowship (No. 12.50.1562.2013). G. M. acknowledges support by the National Science Center (PLCracow) within the Grant Maestro–3 (Dec–2012/06/A/ST5/ 00219). The calculations were performed with the assistance of the Saint Petersburg State University Computer Center and the Chemistry Department of Saint Petersburg State University.pl_PL
dc.language.isoenpl_PL
dc.publisherBeilstein-Institut zur Förderung der Chemischen Wissenschaftenpl_PL
dc.relation.ispartofseriesBeilstein Journal of Organic Chemistry;2015
dc.rightsUznanie autorstwa 3.0 Polska*
dc.rightsUznanie autorstwa 3.0 Polska*
dc.rights.urihttp://creativecommons.org/licenses/by/3.0/pl/*
dc.subjectdiazocarbonyl compoundspl_PL
dc.subject1,3-dipolar cycloadditionpl_PL
dc.subject1,3-oxathiolespl_PL
dc.subjectthiiranespl_PL
dc.subjectthiocarbonyl ylidespl_PL
dc.subjectthioketonespl_PL
dc.titleOn the strong difference in reactivity of acyclic and cyclic diazodiketones with thioketones: experimental results and quantum-chemical interpretationpl_PL
dc.typeArticlepl_PL
dc.page.number504–513pl_PL
dc.contributor.authorAffiliationMereshchenko Andrey S, Institute of Chemistry, Saint Petersburg State Universitypl_PL
dc.contributor.authorAffiliationAlexey, V. Ivanov Institute of Chemistry, Saint Petersburg State Universitypl_PL
dc.contributor.authorAffiliationBaranovskii Viktor I., Institute of Chemistry, Saint Petersburg State Universitypl_PL
dc.contributor.authorAffiliationRodina Ludmila L, Institute of Chemistry, Saint Petersburg State Universitypl_PL
dc.contributor.authorAffiliationNikolaev Valerij A, Institute of Chemistry, Saint Petersburg State Universitypl_PL
dc.contributor.authorAffiliationMlostoń Grzegorz, University of Łódź Faculty of Chemistry,pl_PL
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dc.contributor.authorEmailgmloston@uni.lodz.plpl_PL
dc.identifier.doi10.3762/bjoc.11.57
dc.relation.volume11pl_PL


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