Methyl trifluoromethane sulfonate reaction

Triflucrcrrsethanesuifonate, FNHj FjCSOj, mp subl CA Registry No 42138-65-5. It is prepd by the reaction of N-fluorourethane with trifluoromethanesulfonic acid in methyl chloride (Ref 6). It is more stable than the salts listed above (Ref 6), and upon subln at low press, it dissociates into fluoramine and trifluoromethane-sulfonic acid without further decompn (Ref 7) Refs 1)0. Ruff L. Staub, ZAnorgChem 198, 32 (1931) CA 25, 5105 (1931) 2) O. Ruff... 

The same authors studied the CL of 4,4,-[oxalylbis(trifluoromethylsulfo-nyl)imino]to[4-methylmorphilinium trifluoromethane sulfonate] (METQ) with hydrogen peroxide and a fluorophor in the presence of a, p, y, and heptakis 2,6-di-O-methyl P-cyclodextrin [66], The fluorophors studied were rhodamine B (RH B), 8-aniline-l-naphthalene sulfonic acid (ANS), potassium 2-p-toluidinylnaph-thalene-6-sulfonate (TNS), and fluorescein. It was found that TNS, ANS, and fluorescein show CL intensity enhancement in all cyclodextrins, while the CL of rhodamine B is enhanced in a- and y-cyclodextrin and reduced in P-cyclodextrin medium. The enhancement factors were found in the range of 1.4 for rhodamine B in a-cyclodextrin and 300 for TNS in heptakis 2,6-di-O-methyl P-cyclodextrin. The authors conclude that this enhancement could be attributed to increases in reaction rate, excitation efficiency, and fluorescence efficiency of the emitting species. Inclusion of a reaction intermediate and fluorophore in the cyclodextrin cavity is proposed as one possible mechanism for the observed enhancement. 

Kitazume and Zulfiqar have investigated the Claisen rearrangement of several aromatic allyl ethers in ionic Hquids, catalyzed by scandium(III) trifluoromethane-sulfonate [72]. The reaction initially gave the 2-aUylphenol but this reacted further to give 2-methyl-2,3-dihydrobenzo[b]furan (Scheme 5.1-41). The yields in this reaction were highly dependant on the ionic liquid chosen, with [EDBU][OTf giving the best yields (e.g., 91 % for R = 6-CH3). Reactions in [BMIMjlBFJ and [BMIM][PF j gave low yields (9-12 %). 

Pyruvate ketals can be synthesized [161] by direct condensation of a pyruvate ester with a diol in the presence of a Lewis acid, but this is less preferred because of the electron-withdrawing effect of the adjacent carboxylate group [162,163]. Therefore, several indirect methods for the acetalization have been introduced including condensation with pyruvate derivatives [164,165] or generation of the carboxylate group by oxidation of a suitable precursor [166,167,168,169]. A more efficient route to pyruvic acid acetals starts from silylated diols [170] or by the reaction between diols and methyl pyruvate dialkyl dithioacetal [171,172] activated by methyl triflate, dimethyl(methylthio)sulfonium trifluoromethane sulfonate (DMTST), nitroso tetraflu-oroborate (NOBF4), S02Cl2-trifluoromethanesulfonic acid, or Al-Iodosuccinimide (NIS) and trifluoromethanesulfonic acid [173] (O Scheme 24). 

Mes) is comparable to those found for related Mo (II) NHC complexes [119]. The reaction of the complexes 62 with electrophilic reagents such as trifluoromethane-sulfonic acid or methyl trifluoromethanesulfonate led to the formation of the classical NHC complexes (63 and 64, Scheme 14.32) via a protonation (or alkjdation) of the noncoordinated N atom. The Mo-Ccarbene distance in complexes 63 (R =... 

Polymerization of Methyl 4-(phenylthio)phenyl Sulfoxide. Poly[methyl[4-(phenylthio)phenyl] sulfonium trifluoromethane sulfonate](PPST), A 100 mL, round-bottom flask with a Teflon-covered magnetic stirring bar was charged with methyl 4-(phenylthio)phenyl sulfoxide (1 g, 4 mmol). The flask was cooled to 0 <>C. Trifluoromethane sulfonic acid (5 mL) was added at 0 <>C with stirring. The temperature was increased slowly to room temperature over a period of 0.5 -1 h. The reaction solution turned from colorless to pale blue. The reaction are continued for another 20 h at room temperature. The reaction was then quenched by pouring it into ice water. The precipitated polymer was then chopped in a blender, washed with water, and dried in vacuum at room temperature for 20 h. Yield 1.53 g (100%). IR (KBr, cm-i) 3086,... 

The demethylation of poly[methyl[4-(phcnylthio)phcnyl] sulfonium cation] was carried out in refluxing pyridine. The precursor polymer is completely soluble in the mixture at room temperature, however on reaction a initially white insoluble powder precipitated which was identified as -Methylpyridinium trifluoromethane sulfonate salt. This was isolated quantitatively from the reaction mixture. The resulting polymer has the empirical formula of C6H4S and shows the same IR spectrum and CP/MAS 13C NMR spectra of commercially available PPS. No absorption bands of methyl, sulfone, and sulfoxide bonds are detected in the IR spectrum. 

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