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Reactions of transition metal carbonyl anions with 2-(1-bromoalkylidene)thiazolidin-4-ones: halogenophilic attack or deprotonation
dc.creator | Sazonov, P. K. | |
dc.creator | Džambaski, Zdravko | |
dc.creator | Shtern, M. M. | |
dc.creator | Marković, Rade | |
dc.creator | Beletskaya, I. P. | |
dc.date.accessioned | 2019-01-30T17:28:47Z | |
dc.date.available | 2019-01-30T17:28:47Z | |
dc.date.issued | 2011 | |
dc.identifier.issn | 0040-4039 | |
dc.identifier.uri | https://cer.ihtm.bg.ac.rs/handle/123456789/927 | |
dc.description.abstract | Bromophilic attack by the transition metal carbonyl anion, [Re(CO)(5)]Na (pK(a) = 21.1), on 2-(1-bromoalkylidene)thiazolidin-4-ones is significantly faster than abstraction of an acidic lactam hydrogen (pK(a) similar to 17-18), when the generated carbanion is stabilized by an alpha-CN or alpha-PhCO group. The bromophilic reaction of 2-(1-bromoalkylidene)thiazolidin-4-one, having an alpha-CN electron-withdrawing group, resulted in formation of a new metallacyclic anionic complex. With less reactive vinyl bromides, containing an alpha-CONHPh or alpha-CO(2)Et group, only deprotonation is observed. The role of the metal carbonyl anion is highlighted by a comparison with the 9-methylfluorenide carbanion (pK(a) of 9-methylfluorene is 22.3), which reacts exclusively via a deprotonation pathway. | en |
dc.publisher | Oxford : Pergamon-Elsevier Science Ltd | |
dc.relation | Russian Federation - HLLI-4365.2010.3 | |
dc.relation | RAS - 1-OX | |
dc.relation | info:eu-repo/grantAgreement/MESTD/MPN2006-2010/142007/RS// | |
dc.rights | restrictedAccess | |
dc.source | Tetrahedron Letters | |
dc.subject | Halogenophilic reactions | en |
dc.subject | Proton transfer | en |
dc.subject | 2-(1-Bromoalkylidene)thiazolidin-4-ones | en |
dc.subject | Metal carbonyl anions | en |
dc.title | Reactions of transition metal carbonyl anions with 2-(1-bromoalkylidene)thiazolidin-4-ones: halogenophilic attack or deprotonation | en |
dc.type | article | |
dc.rights.license | ARR | |
dcterms.abstract | Белетскаyа, И. П.; Схтерн, М. М.; Сазонов, П. К.; Марковиц, Р.; Джамбаски, Здравко; | |
dc.citation.volume | 52 | |
dc.citation.issue | 1 | |
dc.citation.spage | 29 | |
dc.citation.epage | 33 | |
dc.citation.other | 52(1): 29-33 | |
dc.citation.rank | M22 | |
dc.identifier.doi | 10.1016/j.tetlet.2010.10.112 | |
dc.identifier.scopus | 2-s2.0-78649872730 | |
dc.identifier.wos | 000286789100005 | |
dc.type.version | publishedVersion |