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2-Alkylidene-4-oxothiazolidine S-oxides: synthesis and stereochemistry
dc.creator | Džambaski, Zdravko | |
dc.creator | Marković, Rade | |
dc.creator | Kleinpeter, Erich | |
dc.creator | Baranac-Stojanović, Marija | |
dc.date.accessioned | 2019-01-30T17:37:44Z | |
dc.date.available | 2019-01-30T17:37:44Z | |
dc.date.issued | 2013 | |
dc.identifier.issn | 0040-4020 | |
dc.identifier.uri | https://cer.ihtm.bg.ac.rs/handle/123456789/1344 | |
dc.description.abstract | A 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.publisher | Oxford : Pergamon-Elsevier Science Ltd | |
dc.relation | info:eu-repo/grantAgreement/MESTD/Basic Research (BR or ON)/172020/RS// | |
dc.relation | Deutscher Akademischer Austauschdienst (DAAD) [504 252 70] | |
dc.rights | restrictedAccess | |
dc.source | Tetrahedron | |
dc.subject | 2-Alkylidene-4-oxothiazolidine | en |
dc.subject | Sulfoxide | en |
dc.subject | Diastereoselectivity | en |
dc.subject | Density functional calculations | en |
dc.subject | CH center dot center dot center dot O hydrogen bonds | en |
dc.title | 2-Alkylidene-4-oxothiazolidine S-oxides: synthesis and stereochemistry | en |
dc.type | article | |
dc.rights.license | ARR | |
dcterms.abstract | Джамбаски, Здравко; Клеинпетер, Ерицх; Марковиц, Раде; Баранац-Стојановиц, Марија; | |
dc.citation.volume | 69 | |
dc.citation.issue | 31 | |
dc.citation.spage | 6436 | |
dc.citation.epage | 6447 | |
dc.citation.other | 69(31): 6436-6447 | |
dc.citation.rank | M21 | |
dc.identifier.doi | 10.1016/j.tet.2013.05.087 | |
dc.identifier.scopus | 2-s2.0-84879225906 | |
dc.identifier.wos | 000321231700013 | |
dc.type.version | publishedVersion |