THIOL ADDITIONS TO 1,4-DIARYLSULFONYL-2-BUTYNES. STEREOCHEMISTRY OF ADDITION AND REGIOSPECIFIC ELIMINATIONS FROM THE ADDUCTS
- 1 August 1985
- journal article
- research article
- Published by Taylor & Francis in Phosphorus and Sulfur and the Related Elements
- Vol. 25 (1) , 1-9
- https://doi.org/10.1080/03086648508074250
Abstract
Thiol additions to 1,4-diarylsulfonyl-2-butynes result in stereoselective formation of 1,4-diarylsulfonyl-2-arylthio-2-butenes with a preponderance of the E isomer over the Z. Contrary to the behaviour of similar adducts from 1-arylsulfonyl-4-(N′-anilino)-2-butynes and 1-arylsulfonyl-4-arylthio-2-butynes, the vinyl sulfides obtained from the diarylsulfonylbutynes undergo facile isomerization under mild base catalysis. A regiospecific elimination followed by readdition is shown to be the mechanism for such isomerizations.Keywords
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