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dc.creatorDžambaski, Zdravko
dc.creatorMarković, Rade
dc.creatorKleinpeter, Erich
dc.creatorBaranac-Stojanović, Marija
dc.date.accessioned2019-01-30T17:37:44Z
dc.date.available2019-01-30T17:37:44Z
dc.date.issued2013
dc.identifier.issn0040-4020
dc.identifier.urihttp://cer.ihtm.bg.ac.rs/handle/123456789/1344
dc.description.abstractA series of 5-unsubstituted and 5-substituted 2-alkylidene-4-oxothiazolidine-S-oxides were synthesized by the sulfur-oxidation with m-CPBA. The stereochemistry of 5-substituted sulfoxides was determined by means of NMR spectroscopy and DFT theoretical calculations. It was found that the thermodynamically less stable anti-isomer was initially formed in the course of the oxidation, but it underwent epimerization to the mixture enriched in the more stable syn-isomer, during the work-up process. The higher stability of syn-isomers is ascribed to the stronger hyperconjugative sigma(C-H)->sigma*(S-O) interaction versus the weaker sigma(C-C)->sigma*(S-O) delocalization in their anti-counterparts and to the existence of intramolecular 1,5-CH center dot center dot center dot C hydrogen bonds.en
dc.publisherPergamon-Elsevier Science Ltd, Oxford
dc.relationinfo:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172020/RS//
dc.relationDeutscher Akademischer Austauschdienst (DAAD) [504 252 70]
dc.rightsrestrictedAccess
dc.sourceTetrahedron
dc.subject2-Alkylidene-4-oxothiazolidineen
dc.subjectSulfoxideen
dc.subjectDiastereoselectivityen
dc.subjectDensity functional calculationsen
dc.subjectCH center dot center dot center dot O hydrogen bondsen
dc.title2-Alkylidene-4-oxothiazolidine S-oxides: synthesis and stereochemistryen
dc.typearticle
dc.rights.licenseARR
dcterms.abstractДжамбаски, Здравко; Клеинпетер, Ерицх; Марковиц, Раде; Баранац-Стојановиц, Марија;
dc.citation.volume69
dc.citation.issue31
dc.citation.spage6436
dc.citation.epage6447
dc.citation.other69(31): 6436-6447
dc.citation.rankM21
dc.identifier.doi10.1016/j.tet.2013.05.087
dc.identifier.rcubConv_2996
dc.identifier.scopus2-s2.0-84879225906
dc.identifier.wos000321231700013
dc.type.versionpublishedVersion


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