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.
Dioxime oxalates, a type of carbonyl oximes, are well-known as clean sources of iminyl radicals that undergo key organic chemistry transformations. A series of dioxime oxalates is reported in this manuscript, obtained by the reaction of the corresponding oximes with oxalyl chloride and Et3N at room temperature. This one-pot method afforded three novel dioxime oxalates and the crystal structure of cyclopentanone dioxime oxalate analysis is also presented.
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