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31.10.2.1.1 Method 1: Nucleophilic Substitution of Arenesulfonimidoyl Halides and Sulfonimidates

DOI: 10.1055/sos-SD-031-00744

Nakamura, S.; Toru, T.Science of Synthesis, (200731861.

The oxidative chlorination of N-phenyl-4-tolylsulfinamides 70 with tert-butyl hypochlorite,[‌260‌] chlorine,[‌261‌] or N-chlorotriazole[‌261‌] affords sulfonimidoyl chlorides 71, which are treated with ethylaluminum dichloride to give the S-ethyl-S-4-tolylsulfoximide 72.[‌262‌] However, this method is restricted to the synthesis of the S-ethylsulfoximide. The reaction of chiral sulfonimidoyl fluorides or sulfonimidates with organolithium or organomagnesium reagents provides a more general preparative method for various S-arylsulfoximides (Scheme 48).[‌263‌]

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