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S,S-Dimethyl-N-(p-toluenesulfonyl)sulfoximine, is used as methylene-transfer agent. The anion adds to carbonyl compounds to give epoxides which can react with a further mole of reagent with ring expansion to give 2,2-disubstituted oxetanes. It is also used as a pharmaceutical intermediate.
CR Johnson.; RA Kirchhoff.; RJ Reischer. Chemistry of sulfoxides and related compounds. XLII. Nucleophilic alkylidene transfer reagents. Anions of N-(p-tolylsulfonyl) sulfoximines. J. Am. Chem. Soc. 197395 (13), 4287-4291.
SL Huang.; D Swern. Oxidation of N-acyl-, N-sulfonyl-, and N-arylsulfilimines to sulfoximines by m-chloroperoxybenzoate anion. The Journal of Organic Chemistry. 197944 (14), 2510-2513.
Methylene-transfer agent. For reviews, see: Acc. Chem. Res., 6, 341 (1973); Chem. Soc. Rev., 4, 189 (1975). The anion adds to carbonyl compounds to give epoxides which can react with a further mole of reagent with ring expansion to give 2,2-disubstituted oxetanes: J. Am. Chem. Soc., 101, 6135 (1979); 105, 252 (1983):