B. S. Thyagarajan, K. Majumdar, D. K. Bates
Feb 1, 1975
Citations
0
Influential Citations
12
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
The mercuric ion-catalyzed hydration of 1,4-bis(arylthio)-2-butynes and 1-aryloxy-4-arylthio-2-butynes was studied. The 1,4-bis(arylsulfonyl)-2-butynes afforded 1,4-bis(arylsulfonyl)-2-butanones (7). The 1,4-bis(arylthio)-2-butynes afforded a variety of products in acetic acid among which were: 1,4-bis(arylthiomethyl)vinyl acetate (18); 1,4-bis(arylthio)-2-butanone (15); 1-(arylthio)-3-buten-2-one (16); and 1-(arylthio)-4-acetoxy-2-butanone (17). Ketone 15 eliminates arylthiol in an acidic medium yielding 16 which undergoes Michael addition of solvent to give 17. Treatment of 7 with base in the presence of a nucleophile (ArSH) analogously leads to elimination of arylsulfinic acid, followed by Michael addition of arylthiol. Hydration of 5 in methanol cleanly gave 1-(arylthio)-4-methoxy-2-butanones (19). In contrast, 1-aryloxy-4-arylthio-24)utynes afforded chromenes (8) by intramolecular cyclization. No thiochromenes were formed in any of the examples investigated.