Tetrahedron p. 2475 - 2484 (1986)
Update date:2022-07-31
Topics:
Julia, Marc
Lauron, Helene
Stacino, Jean-Pierre
Verpeaux, Jean-Noel
Jeannin, Yves
Dromzee, Yves
The stereospecific hydrogenolysis of vinylic sulfones by sodium dithionite in a protic medium proceeds by addition of HSO2- to give an intermediate which could be isolated after alkylation in situ to a 1,2-bissulfone.The mechanism is therefore of the β-addition-elimination type.In the case of E-2-benzenesulfonyl-2-butene and ethyl iodide a single crystalline diastereoisomer was obtained and shown to have the threo configuration by X-ray crystallography.The addition step follows the syn and the elimination step the anti stereochemistry, thus accounting for the overall retention of configuration observed.
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