Thiol Additions To Dissymmetrical 1,4-Diary Sulfonyl-2-Butynes Regioselectivity And Stereoselectivity
- 1 January 1986
- journal article
- research article
- Published by Taylor & Francis in Phosphorus and Sulfur and the Related Elements
- Vol. 26 (3) , 275-284
- https://doi.org/10.1080/03086648608084581
Abstract
Regioselectivity is restored in the addition of thiols to 1,4-diarylsulfonyl-2-butynes based on differing electron-demands of the substituents on the aromatic rings attached to the butynyl sulfones. Kinetic control of addition leading to preponderant formation of the less stable vinyl sulfide with an E geometry is observed. Thermodynamic stability favors the Z isomer of the vinyl sulfide. The results are consistent with and confirm the rationale proposed earlier, implicating the intermediacy of an allene.Keywords
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