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dc.creatorLorenc, Ljubinka
dc.creatorGašić, Miroslav J.
dc.creatorDabović, Milan
dc.creatorVuletić, N
dc.creatorMihailović, Mihailo Lj.
dc.date.accessioned2019-04-26T11:37:37Z
dc.date.available2019-04-26T11:37:37Z
dc.date.issued1979
dc.identifier.issn0040-4020
dc.identifier.urihttp://cer.ihtm.bg.ac.rs/handle/123456789/2700
dc.description.abstractThe solvolysis of (Z)- and (E)-3β-acyloxy-5,10-seco-1(10)-cholesten-5β-ol p-nitrobenzoates 4 and 5 has been investigated and compared with the solvolytic reactivity of the epimeric (Z)- and (E)-5α-p-nitrobenzoates 1 and 2, as well as of the reference compound, i.e. the 1,10-saturated 5α-p-nitrobenzoate. Kinetic data and product analysis revealed that the relative spatial orientation of the 1(10)-olefinic double bond and the chiral center at C(5) in the 10-membered ring, which these secosteroidal 5-p-nitrobenzoates can adopt in the transition state, is the main factor which determines their solvolytic behaviour, so that the esters 1,2 and 5 solvolyse with transannular double bond participation, while such an interaction is not present in the case of the (Z)-5β-ester 4. © 1979.
dc.publisherPergamon Press
dc.relationSerbian Republic Research Fund
dc.relationSerbian Academy of Science and Arts
dc.rightsrestrictedAccess
dc.sourceTetrahedron
dc.sourceTetrahedron
dc.titleStructure-reactivity relationship in the solvolysis of 5,10-secosteroidal 5-p-nitrobenzoates
dc.typearticleen
dc.rights.licenseARR
dcterms.abstractГашић, М. Ј.; Вулетић, Н; Михаиловић, М. Љ.; Лоренц, Љубинка; Дабовић, Милан;
dc.rights.holderElsevier
dc.citation.volume35
dc.citation.issue20
dc.citation.spage2445
dc.citation.epage2452
dc.identifier.doi10.1016/S0040-4020(01)93762-7
dc.identifier.scopus2-s2.0-49249149067
dc.identifier.scopus2-s2.0-49249149067
dc.type.versionpublishedVersion


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