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Title of article :
Stereoisomerization of α-hydroxy-β-sulfenyl-α,β-dimethyl naphthoquinones controlled by nonbonded sulfur–oxygen interactions
Author/Authors :
Antonio Latorre، نويسنده , , Santiago Rodr?guez، نويسنده , , Amit Jain، نويسنده , , Florenci V. Gonz?lez، نويسنده , , José A. Mata، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2013
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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.
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