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39.4.2.2.4 Method 4: Oxidation of Organic Halides and Sulfonates with Dimethyl Sulfoxide

DOI: 10.1055/sos-SD-039-00359

García Ruano, J. L.; Cid, M. B.; Martín-Castro, A. M.; Alemán, J.Science of Synthesis, (200839348.

The reactions of organic halides and sulfonates with dimethyl sulfoxide proceed by route B as depicted in Scheme 117 in Section 39.4.2.2, via formation of an alkoxydimethylsulfonium salt by direct nucleophilic displacement of a leaving group by dimethyl sulfoxide. High yields are reported in the oxidation of α-halo esters or acids,[‌610‌] phenacyl halides,[‌566‌,‌611‌] benzyl halides, primary sulfonates,[‌612‌,‌613‌] primary iodides,[‌614‌] a limited number of secondary halides,[‌615‌,‌616‌] and secondary 4-toluenesulfonates.[‌617‌‌619‌]

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