STEREOSELECTIVE ADDITION OF ARENE THIOLS TO 1,4-DISUBSTITUTED-2-BUTYNES
- 1 January 1985
- journal article
- research article
- Published by Taylor & Francis in Phosphorus and Sulfur and the Related Elements
- Vol. 21 (3) , 357-366
- https://doi.org/10.1080/03086648508077679
Abstract
Base-catalyzed addition of arene thiols to 1,4-disubstituted-2-butynes (1 and 2) afford the β,γ-unsaturated sulfones (8E and 8Z). In addition to the regiospecificity observed, the vinyl sulfides are formed with a high degree of stereoselectivity. Product formation through a less-hindered approach by the nucleophile appears to favor the E over the Z isomer, consistently in all the 11 cases investigated.Keywords
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