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Reduction of Sulfoxides in Multigram Scale, an Alternative to the Use of Chlorinated Solvents

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Abstract:

In this manuscript, we describe the use of ethyl vinyl ether/oxalyl chloride as the reducing mixture for sulfoxides. The reaction is based on the high electrophilic character of chlorosulfonium salts, formed in situ by the reaction of oxalyl chloride and the sulfoxide. Thereafter, the nucleophilic vinyl ether acts as a chlorine scavenger, affording the corresponding sulfide. The method is applicable on a big scale and may be applied to highly functionalized sulfoxides. Chromatographic purification is only needed in exceptional cases of unstable substrates, and the final sulfide or the corresponding salt is usually obtained after simple evaporation of volatiles. The sole contaminants of this method are carbon dioxide, carbon monoxide and small (five-carbon maximum) aldol products, which are formed during the reaction process.

Tópico:

Chemical Synthesis and Reactions

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Citations: 3
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Información de la Fuente:

SCImago Journal & Country Rank
FuenteProcesses
Cuartil año de publicaciónNo disponible
Volumen10
Issue6
Páginas1115 - 1115
pISSNNo disponible
ISSN2227-9717

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