Reactivity of 1-phenylsulfinyl-2-phenylsulfanylethylene (SOSE) with O-nucleophiles generated by potassium tert-butoxide
L Pellizzaro, E Cabianca, A Tatibouët, P Padovan…
Index: Pellizzaro, Leonardo; Cabianca, Elena; Tatibouet, Arnaud; Padovan, Pierluigi; Fabris, Fabrizio; Rollin, Patrick; De Lucchi, Ottorino Tetrahedron Letters, 2007 , vol. 48, # 21 p. 3699 - 3703
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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: ...
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