Paper
Additions of nucleophiles to 3-oxo-2,3-dihydrothiophene 1,1-dioxides. Formation of vinyl sulfides, thioacetals and enaminones
Published Jan 1, 1999 · N. U. Hofsløkken, L. Skattebol
Journal of The Chemical Society-perkin Transactions 1
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Abstract
3-Oxo-2,3-dihydrothiophene 1,1-dioxide (1a) was prepared by oxidation of the commercially available 3-methoxythiophene with dimethyldioxirane. Some other substituted 3-methoxythiophene derivatives were oxidized as well. Although the yields of these reactions were low, the one-step method is preferred to the current literature procedures. 3-Oxo-2,3-dihydrothiophene 1,1-dioxide derivatives reacted with sulfur and nitrogen nucleophiles. Reactions took place with extrusion of sulfur dioxide even at room temperature. High yields of vinyl sulfides, thioacetals, bis-thioacetals, and enaminones were obtained from these reactions.
This study presents a one-step method for preparing 3-oxo-2,3-dihydrothiophene 1,1-dioxide derivatives, which can be used to produce high yields of vinyl sulfides, thioacetals, bis-thioacetals,
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