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Stereoisomerization of α-hydroxy-β-sulfenyl-α,β-dimethyl naphthoquinones controlled by nonbonded sulfur–oxygen interactions
dc.contributor.author | Latorre, Antonio | |
dc.contributor.author | Rodríguez, Santiago | |
dc.contributor.author | Jain, Amit | |
dc.contributor.author | González, Florenci | |
dc.contributor.author | Mata Martínez, Jose A | |
dc.date.accessioned | 2014-03-31T07:41:00Z | |
dc.date.available | 2014-03-31T07:41:00Z | |
dc.date.issued | 2013-03 | |
dc.identifier.citation | LATORRE, 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.uri | http://hdl.handle.net/10234/88871 | |
dc.description.abstract | The 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.extent | 3 p. | ca_CA |
dc.format.mimetype | application/pdf | ca_CA |
dc.language.iso | eng | ca_CA |
dc.publisher | Elsevier | ca_CA |
dc.relation.isPartOf | Tetrahedron Volume 69, Issue 9, 4 March 2013, Pages 2098–2101 | ca_CA |
dc.rights.uri | http://rightsstatements.org/vocab/CNE/1.0/ | * |
dc.subject | naphthoquinone | ca_CA |
dc.subject | oxygen | ca_CA |
dc.subject | sulfur | ca_CA |
dc.subject | chemical bond | ca_CA |
dc.subject | crystal structure | ca_CA |
dc.subject | isomer | ca_CA |
dc.subject | isomerization | ca_CA |
dc.subject | stereochemistry | ca_CA |
dc.title | Stereoisomerization of α-hydroxy-β-sulfenyl-α,β-dimethyl naphthoquinones controlled by nonbonded sulfur–oxygen interactions | ca_CA |
dc.type | info:eu-repo/semantics/article | ca_CA |
dc.identifier.doi | http://dx.doi.org/10.1016/j.tet.2013.01.033 | |
dc.rights.accessRights | info:eu-repo/semantics/openAccess | ca_CA |
dc.relation.publisherVersion | http://www.sciencedirect.com/science/article/pii/S0040402013000744 | ca_CA |
dc.type.version | info:eu-repo/semantics/acceptedVersion |
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