Organic synthesis with sulfones. XXXVIII: On the mechanism of the stereospecific hydrogenolysis of vinylic sulfones by sodium dithionite
作者： Marc Julia , Hélène Lauron , Jean-Pierre Stacino , Jean-Noël Verpeaux , Yves Jeannin
DOI: 10.1016/0040-4020(86)80011-4
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摘要: Abstract The stereospecific hydrogenolysis of vinylic sulfones by sodium dithionite in a protic medium proceeds addition HSO2 to give an intermediate which could be isolated after alkylation situ 1,2-bissulfone. mechanism is therefore the β-addition-elimination type. In case E-2-benzenesulfonyl-2-butene and ethyl iodide single crystalline diastereoisomer was obtained shown have threo configuration X-ray crystallography. step follows syn elimination anti stereochemistry, thus accounting for overall retention observed.
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