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dc.contributor.authorLatorre, Antonio
dc.contributor.authorRodríguez, Santiago
dc.contributor.authorJain, Amit
dc.contributor.authorGonzález, Florenci
dc.contributor.authorMata Martínez, Jose A
dc.date.accessioned2014-03-31T07:41:00Z
dc.date.available2014-03-31T07:41:00Z
dc.date.issued2013-03
dc.identifier.citationLATORRE, Antonio, et al. Stereoisomerization of α-hydroxy-β-sulfenyl-α, β-dimethyl naphthoquinones controlled by nonbonded sulfur–oxygen interactions. Tetrahedron, 2013, 69.9: 2098-2101.ca_CA
dc.identifier.urihttp://hdl.handle.net/10234/88871
dc.description.abstractThe anti α-hydroxy-β-sulfenyl-α,β-dimethyl naphthoquinones isomerize in basic media into syn/anti mixtures of isomers, giving the syn isomer as the major product. Conversely, anti α-hydroxy-β-alkoxy-α,β-dimethyl naphthoquinones isomerize to furnish the anti isomer as the major product. The crystal structure of syn α-hydroxy-β-phenylsulfenyl-α,β-dimethyl naphthoquinone has been determined. The X-ray and experimental work demonstrated that an attractive 1,4 intramolecular interaction of divalent sulfur with hydroxyl oxygen is the driving force for the aforementioned stereochemical preference.ca_CA
dc.format.extent3 p.ca_CA
dc.format.mimetypeapplication/pdfca_CA
dc.language.isoengca_CA
dc.publisherElsevierca_CA
dc.relation.isPartOfTetrahedron Volume 69, Issue 9, 4 March 2013, Pages 2098–2101ca_CA
dc.rights.urihttp://rightsstatements.org/vocab/CNE/1.0/*
dc.subjectnaphthoquinoneca_CA
dc.subjectoxygenca_CA
dc.subjectsulfurca_CA
dc.subjectchemical bondca_CA
dc.subjectcrystal structureca_CA
dc.subjectisomerca_CA
dc.subjectisomerizationca_CA
dc.subjectstereochemistryca_CA
dc.titleStereoisomerization of α-hydroxy-β-sulfenyl-α,β-dimethyl naphthoquinones controlled by nonbonded sulfur–oxygen interactionsca_CA
dc.typeinfo:eu-repo/semantics/articleca_CA
dc.identifier.doihttp://dx.doi.org/10.1016/j.tet.2013.01.033
dc.rights.accessRightsinfo:eu-repo/semantics/openAccessca_CA
dc.relation.publisherVersionhttp://www.sciencedirect.com/science/article/pii/S0040402013000744ca_CA
dc.type.versioninfo:eu-repo/semantics/acceptedVersion


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