Synthesis of Vinyl Sulfides using Selenium Ionic Liquid

Synthesis of Vinyl Sulfides using Selenium Ionic Liquid

Thurow, Samuel; Mendes, Samuel R.; Alves, Diego; Perin, Gelson; Jacob, Raquel G.; Lenardão, Eder J.

Abstract:

Vinyl sulfides are very versatile and useful intermediates in organic synthesis and there are several compounds of natural occurrence bearing the vinyl sulfide group isolated from bloming plants of the tribe Heliantheae (Asteraceae). In addition, vinyl sulfides can be converted into the corresponding aldehyde, ketone or carboxylic acid or ester by acid hydrolysis or through the thio- Claisen rearrangement. On the other hand, ionic liquids (ILs) constitute an interesting alternative to solvents in organic synthesis. Because product isolation or catalyst recycling is very easy in ILs and, in some cases, rate accelerations and/or selectivity improvements are also observed, they are regarded as environmentally friendly green solvents. Due our continuing interest in the synthesis and applications of organochalcogenium chemistry and in new applications for selenium-based ionic liquids, we decide to study the use of [bmim][SeO2(OCH3)] for the synthesis of vinyl sulfides by hydrothiolation of terminal alkynes.

Vinyl sulfides are very versatile and useful intermediates in organic synthesis and there are several compounds of natural occurrence bearing the vinyl sulfide group isolated from bloming plants of the tribe Heliantheae (Asteraceae). In addition, vinyl sulfides can be converted into the corresponding aldehyde, ketone or carboxylic acid or ester by acid hydrolysis or through the thio- Claisen rearrangement. On the other hand, ionic liquids (ILs) constitute an interesting alternative to solvents in organic synthesis. Because product isolation or catalyst recycling is very easy in ILs and, in some cases, rate accelerations and/or selectivity improvements are also observed, they are regarded as environmentally friendly green solvents. Due our continuing interest in the synthesis and applications of organochalcogenium chemistry and in new applications for selenium-based ionic liquids, we decide to study the use of [bmim][SeO2(OCH3)] for the synthesis of vinyl sulfides by hydrothiolation of terminal alkynes.

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DOI: 10.5151/chempro-14bmos-R0143-2

Referências bibliográficas

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Como citar:

Thurow, Samuel; Mendes, Samuel R.; Alves, Diego; Perin, Gelson; Jacob, Raquel G.; Lenardão, Eder J.; "Synthesis of Vinyl Sulfides using Selenium Ionic Liquid", p-143-143. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0143-2