Stereoisomerization of α-hydroxy-β-sulfenyl-α,β-dimethyl naphthoquinones controlled by nonbonded sulfur–oxygen interactions
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Show full item recordcomunitat-uji-handle:10234/9
comunitat-uji-handle2:10234/7033
comunitat-uji-handle3:10234/8618
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INVESTIGACIONMetadata
Title
Stereoisomerization of α-hydroxy-β-sulfenyl-α,β-dimethyl naphthoquinones controlled by nonbonded sulfur–oxygen interactionsAuthor (s)
Date
2013-03Publisher
ElsevierBibliographic 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.Type
info:eu-repo/semantics/articlePublisher version
http://www.sciencedirect.com/science/article/pii/S0040402013000744Version
info:eu-repo/semantics/acceptedVersionSubject
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 ... [+]
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. [-]
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Tetrahedron Volume 69, Issue 9, 4 March 2013, Pages 2098–2101Rights
http://rightsstatements.org/vocab/CNE/1.0/
info:eu-repo/semantics/openAccess
info:eu-repo/semantics/openAccess
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