107398-31-2Relevant academic research and scientific papers
ORGANIC SYNTHESIS WITH SULFONES. XXXVIII. ON THE MECHANISM OF THE STEREOSPECIFIC HYDROGENOLYSIS OF VINYLIC SULFONES BY SODIUM DITHIONITE.
Julia, Marc,Lauron, Helene,Stacino, Jean-Pierre,Verpeaux, Jean-Noel,Jeannin, Yves,Dromzee, Yves
, p. 2475 - 2484 (2007/10/02)
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.
