Sodium triflate

Data reported for the protolysis constant of water in sodium triflate media are listed in Table 5.29. The data have been acquired across a temperature range of 25-250 °C, with the data reported by Palmer and Drummond (1988). 

Few data have been reported for the osmotic coefficient data of sodium triflate solutions. Rard, Palmer and Albright (2003) gave data for only two temperatures, 25 and 50 °C. Equation (5.18) was used to determine water activity data from these osmotic coefficient data. At these two temperatures, the dependence of the water activity data on ionic strength in sodium triflate solutions can be described by Eq. (5.19), and the values derived for and 2 are listed in Table 5.30. 

The data listed in Table 5.30 can be described by Eq. (5.22), but, because there are data at only two temperatures, the values of 2 and must be assigned values 

On the basis of the individual ion interaction parameters already derived for (Na, OH ) (see Table 5.5), those for (H+, triflate ) are 

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Y(03SCF3)3 to afford a monoaminoalkylation product in good yield in aqueous media.40 Zinc tetrafluoroborate is also highly effective for such couplings in aqueous THF.41 Kobayashi also reported a Mannich-type reaction of imines with silyl enolates catalyzed by neutral salts such as sodium triflate in water as a suspension medium. Unusual kinetic behavior indicates that the presence of the Mannich adduct facilitates the rate of its formation.42... 

Similar aza-Diels-Alder reactions of Danishefsky s diene with imines or aldehydes and amines in water took place smoothly under neutral conditions in the presence of a catalytic amount of an alkaline salt such as sodium triflate or sodium tetraphenylborate to afford dihydro-4-pyridones in high yields (Eq. 12.49).117 Antibodies have also been found to catalyze hetero-Diels-Alder reactions.118... 

Little information has appeared on derivatives of [l,2,3,5]thiatriazolopyridines as mentioned also in CHEC-11(1996) <1996CHEC-II(8)405>. In a recent study, the thermal decomposition of the sulfoxide derivative 44 in methanol in the presence of sodium triflate was investigated <1996JFC161> (Scheme 13). After a prolonged reflux, two products 2-pyridyl triflate 46a and 2-methoxypyridine 46b, was isolated in 34% and 16% yields, respectively. The authors concluded that the first step of this transformation is a thermal ring opening of 45 to a carbene intermediate. 

Sodium trifluoromethanesulfonate (triflate) was prepared from trifluoromethanesulfonic acid (Aldrich Chemical Company, Inc.) as follows A solution of 26.5 g (0.66 mol) of sodium hydroxide in 50 mL of water was added dropwise to 100 g (0.67 mol) of triflic acid chilled in an ice bath. The solution was concentrated to dryness with a rotary evaporator, and the residual solid was recrystallized from 65 mL of acetonitrile. The collected solid was dried at 80°C under vacuum for 24 hr to give 90 g of pure sodium triflate. 

Sodium triflate Methanesulfonic acid, trifluoro-, sodium salt (8,9) (2926-30-9) Trifluoromethanesulfonic add Methanesulfonic acid, trifluoro- (8,9) (1493-13-6) Fluorine (8,9) (7782-41-4)... 

Most interesting are the effects of salt complexation on the mesomorphic behavior of liquid crystalline crown ethers and liquid crystalline crown ether polymers. Sodium triflate was added to poly(17) [34] and poly(25) (Scheme 14) [39]. The enantiotropic nematic and smectic phases of poly(17) were changed dramatically [40]. With increasing amounts of salt, the clearing temperatures are shifted to higher values while the melting transition increases only slightly. 

Although a number of electrophilic fluorinating reagents are known, most are toxic, unstable, and difficult to handle. These new, stable N-fluoropyridinium salts are readily obtained in 60-80% yield by reaction of a pyridine with F2/N2(l/9) in CH3CN in the presence of sodium triflate. 

The preparation of a cubic phase with supramolecular chirality was achieved using a branched folic acid derivative incorporating glutamic acid residues (Fig. 11) as the source of chirality [93]. The pterin rings of folic acid residues are able to form a cyclic tetramer as a result of two hydrogen bonds between the components. Depending on the number of carbon atoms in the alkyl substituents, the compounds form columnar phases over a wide temperature range, and for 8 and 9 form cubic phases at temperatures above 130 °C. Addition of sodium triflate stabilises the cubic phase for 7, and the salt is incorporated into the other mesophases. It was implied that the cation resides between stacked tetramers. Supramolecular chirality is expressed for both the columnar and the cubic phases, as revealed by vari-... 

The salt is prepared by reaction of pyridine with sodium triflate and fluorine diluted in nitrogen or helium (caution F2 is very toxic and corrosive). 

Thiosulfonic S-esters. L sodium triflate is added, RSTf i lodination. Efficient at and heteroarenes by PhI(OCOC Nucleophilic aromatic suh alkoxyarenes generates electro MejSiNj and 1,3-diketones. 

Thiosulfonk S-esters. Disulfides undergo oxidation to give RSOjSR. When sodium triflate is added, RSTf are formed. ... 

Fig. 4. Normal pulse polarogram of Yb (L) in 0.3 M sodium triflate acetonitrile solution. Negative potentials (V vs SCE) are plotted to the right and reduction currents are plotted upward. The inset shows a plot of —E vs log 0 l —i//) for the normal pulse polarogram.

Ion-pairing effects on vis-cosity/conductance relations in Raman-characterized polymer electrolytes lithium perchlorate and sodium triflate in PPG(4000). J. Phys. Chem., 95 (23), 9464-9469. 

The aza-Diels-Alder reaction of imines with diene of Danishefsky is an important route to 2,3-dihydro-4-pyridones. A number of Lewis acids have been used to catalyze the reaction in organic solvents. In water the reaction was realized by acid catalysis via iminium salts or by Bronsted acids. The montmorillonite K-10 catalyzed this cycloaddition in water or in aqueous acetonitrile in excellent yield. Recently Kobayashi has performed the reaction in water at room temperature under neutral conditions in two (imine - - diene) or three (aldehyde -b amine -b diene) component versions by using sodium triflate as catalyst. Imine intermediates from the indium-mediated reaction, in aqueous medium at 50° C, between aromatic nitro compounds and 2,3-dihydrofuran undergo aza-Diels-Alder cycloadditions to give tetrahydroquinoline derivatives in good overall yields. ... 

Kobayashi and coworkers showed that Lewis add surfactant-combined catalysts such as scandium tris(dodecyl sulfate), Sc(03SCi2H25)3, or copper bis(dodecyl sulfate), Cu(03SCi2H25)2, were efficient catalysts for the three-component Mannich-type reaction, with 73-95% yield being obtained in neat water.Neutral salts such as sodium triflate and sodium iodide catalyzed the condensation reaction in water between preformed imines and silicon enolates, or the three-component Mannich-type reaction using aromatic amines, with 49-93% yields and 0-80% diastereoselectivities. Mechanistic studies indicated that both sodium triflate and the Mannich adduct itself cooperatively promote the reaction. 

Nitrile and isonitrile compounds were prepared by the reaction of complexes [Re(CO)3(N-RIm)2(OTf)] with pivalonitrile or ferf-butylisocyanide and the salt NaBAr 4 in dichloromethane. Employing the latter as a triflate abstractor is based on the low solubility of sodium triflate in dichloromethane and is needed to achieve the displacement of triflate from the cationic complex by the poor donor nitrile, or by the low-nucleophilic isonitrile. 

Stevens and Schanz (174) used differential scanning calorimetry to study the increase in Tg for complexes of a 4000-molecular-weight polypropylene glycol and lithium perchlorate, lithium triflate, and sodium triflate at various salt concentra-... 

YORK s, FRECH R, SNOW A and GLATZHOFER D, A comparative vibrational spec-troscopicstudy of lithium triflate and sodium triflate in linear poly(ethylenimine) , Electrochim Acta, 2001, 46,1533-1537... 

Table 5.33 contains a comparison of protolysis constant data obtained for sodium triflate data using Eqs. (5.17) and (5.20)-(5.24) with those reported in... 

Table 5.30 Values of a, and Qj in Eq. (5.19) at various temperatures for sodium triflate solutions.

Table 5.32 Values of At, to Ae23 in Eqs. (5.23) and (5.24) for sodium triflate solutions. ...

The ionic strength dependence of the protolysis constant of water in sodium triflate media and at 25 C is illustrated in Figure 5.29. The solid line on the figure is derived from the use of Eq. (5.17) with logliC, ° = -13.994 0.014. From use of the equation, the following ion interaction parameters are derived ... 

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