ChemInform Abstract: N‐Trifluoromethylsulfonyl‐S‐trifluoromethyl‐S‐arylsulfoximides.

Abstract

146ChemInform Abstract The imines (I) are converted to their sodium salts (II). These are then converted to the title compounds (III) by reaction with (CF3SO2)2O or with CF3SO2Cl. The group attached to the aryl moiety R of the titlecompounds (III), is, by its electronic nature, a very strong electron acceptor, which exerts the same effect on the aryl group as do two nitro groups in the ortho and para positions of the a romatic ring. Diazotization of the amine (IV) followed by treatment with PhNMe2 affords the diazo compound (V), which displays negative halochromism, i.e. the absorption maxima are shifted to greater wavelengths on going from acidic to neutral media.

Vicarious Nucleophilic Substitutions of Hydrogen in 1,1,1‐Trifluoro‐N‐[oxido(phenyl)(trifluoromethyl)‐λ4‐sulfanylidene]methanesulfonamide

“…Silica gel (230-400 mesh) was used for column chromatography. [15] Reactions of 1 and 2a-f: To a stirred solution of tBuOK (337 mg, 3 mmol) in DMF (2 mL) at -30°C and under an argon atmosphere was added, by cannula, a solution of CH acid 2a-g (1 mmol) in DMF (2 mL) and a solution of electrophile 1 (341 mg, 1 mmol) in DMF (1 mL). After 10 min stirring, the mixture was poured into cooled 3 % aqueous HCl (100 mL).…”

Divergent Synthesis of 1,2-Benzo[e]thiazine and Benzo[d]thiazole Analogues Containing a S-Trifluoromethyl Sulfoximine Group: Preparation and New Properties of the Adachi Reagent

“…11 To the best of our knowledge no other synthesis has been proposed in the literature. 12 We chose the molecule 5n as a model substrate owing to its high yielding and straightforward synthesis starting from iodo sulfoximine 1. Ozonolysis of the exocyclic double bond of 5n gave rise to the target compound 6 in a reasonable yield.…”

Fluorinated sulfoximines: syntheses, properties and applications

“…As attempts to apply the standard protocol for sulfoxide iminations with sodium azide in sulfuric acid failed in cases of S-aryl S-CF 3 derivatives, oleum (24%) was applied as solvent instead of sulfuric acid, and in this manner the desired S-aryl S-CF 3 sulfoximines were accessed in up to 96% yield. 30 A similar strategy was then applied to S-alkyl S-CF 3 and S-alkyl S-C 8 F 17 sulfoxides 71, which led to the corresponding sulfoximines 72 in high yields (Scheme 15). 31 The procedure with sodium azide in oleum was also used for the syntheses of 1-oxo-1-trifluoromethyl-1l 6 -benzo[d]isothiazol-3-one (73a), 1-trifluoro-methyl-benzo[1,3,2]dithiazole 1,3,3-trioxide (73b), and acyclic sulfoximines 74a and 74b (Scheme 16).…”