Author/Authors :
Pellizzaro، نويسنده , , Leonardo and Cabianca، نويسنده , , Elena and Tatibouët، نويسنده , , Arnaud and Padovan، نويسنده , , Pierluigi and Fabris، نويسنده , , Fabrizio and Rollin، نويسنده , , Patrick and De Lucchi، نويسنده , , Ottorino، نويسنده ,
Abstract :
E-1-Phenylsulfinyl-2-phenylsulfanylethylene (E-SOSE) reacts with O-nucleophiles generated by means of t-BuOK via an addition–elimination mechanism, thus affording the product of substitution of the phenylsulfanyl group in a stereo-conservative process. When used alone, the strongly basic and hindered tert-butoxide brings about elimination of either the phenylthiolate or phenylsulfinate groups. Z-SOSE is much more prone to elimination: either with t-BuOK alone or with other O-nucleophiles generated by t-BuOK, it always leads to products derived from elimination. Other alkaline tert-butoxides or other bases appear not as effective in generating species nucleophilic enough to react with E-SOSE.
