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Synthesis, structure, and reactions of secosteroids containing a medium-sized ring. Part 17. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 3-tosylates
dc.creator | Lorenc, Ljubinka | |
dc.creator | Gašić, Miroslav J. | |
dc.creator | Juranić, Ivan | |
dc.creator | Dabović, Milan | |
dc.creator | Minailović, M. Lj. | |
dc.date.accessioned | 2019-04-26T16:16:11Z | |
dc.date.available | 2019-04-26T16:16:11Z | |
dc.date.issued | 1980 | |
dc.identifier.issn | 1472779X | |
dc.identifier.uri | https://cer.ihtm.bg.ac.rs/handle/123456789/2709 | |
dc.description.abstract | Kinetic measurements of the solvolysis of (Z)-3α- and (Z)-3β-, and (E)-3α- and (E)-3β-tosyloxy-5,10-secocholest-1(10)-en-5-ones in buffered aqueous acetone (90 : 10 v/v) reveal that the (Z)-3α-, (E)-3α-, and (E)-3β-tosylates are solvolysed according to a first-order rate law (the relative rates being ca. 1 : 3 : 8), while the (Z)-3β-ester, under the same conditions, reacts at a much slower rate by a complex mechanism, the kinetics of which are best approximated by a second-order law. These data and product analysis indicate that the former three esters are solvolysed with considerable double bond participation [resulting in the case of the (E)-3-esters in intramolecular cyclopropane ring closure], and that this interaction is unimportant for the (Z)-3β-tosylate. On the basis of conformational analysis of the starting tosylates and stereoelectronic requirements for homoallylic interaction, a possible mechanistic pathway for these solvolyses is proposed. | en |
dc.publisher | Royal Society of Chemistry | |
dc.relation | Serbian Republic Research Fund | |
dc.relation | Serbian Academy of Sciences and Arts | |
dc.rights | restrictedAccess | |
dc.source | Journal of the Chemical Society, Perkin Transactions 2 | |
dc.title | Synthesis, structure, and reactions of secosteroids containing a medium-sized ring. Part 17. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 3-tosylates | en |
dc.type | article | en |
dc.rights.license | ARR | |
dcterms.abstract | Лоренц, Љубинка; Минаиловић, М. Љ.; Дабовић, М.; Јуранић, Иван; Гашић, М. Ј.; | |
dc.rights.holder | Royal Society of Chemistry | |
dc.citation.issue | 9 | |
dc.citation.spage | 1356 | |
dc.citation.epage | 1365 | |
dc.identifier.rcub | https://hdl.handle.net/21.15107/rcub_cer_2709 | |
dc.identifier.scopus | 2-s2.0-37049113652 | |
dc.type.version | publishedVersion |