| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5280519 | Tetrahedron Letters | 2007 | 5 Pages |
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.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Leonardo Pellizzaro, Elena Cabianca, Arnaud Tatibouët, Pierluigi Padovan, Fabrizio Fabris, Patrick Rollin, Ottorino De Lucchi,