ChemInform Abstract: Divinyl Sulfoxide. Part 10. Reaction of Divinyl Sulfoxide with Acetoacetic Ester and Malonic Ester.

Abstract

113ChemInform Abstract The reaction between divinyl sulfoxide (I) and ethyl acetoacetate (IIa) or diethyl malonate (IIb) affords a mixture of the hitherto unknown acyclic sulfoxides (III)-(V) and the cyclic sulfoxides (VI). The yields of each of the components vary depending on the reaction conditions. Thermolysis of (VI) affords the functionalized dienes (VII). The compounds (III)-(VII) may be employed as starting materials for a variety of syntheses.

Divinyl Sulfoxide: XI. Selective Addition of Carbonodithioate Anions to Divinyl Sulfoxide in the Water-Benzene System

“…For example, the available divinyl sulfoxide [5] reacts with water (hydroxide anion [1], amines [6], alcohols (alkoxide anions) [7], thiols (thiolate anions) [8], and CH-acid anions [9] in the presence of proton carriers to form, depending on reagent ratio, mono-or diadducts in high or good yields. At the same time, no information on the possibility of reaction of vinyl sulfoxides with alkali metal carbonothioates is available, even though were this reaction accomplished, the reactivity of the vinylsulfinyl group would be better understood.…”