Ethyl trifluoromethanesulfonate

Ethyl trifluoromethanesulfonate [425-75-2] M 178.1, b 115 /atm, 118-120 /atm, d 1.378, Hp 1.336. The ester reacts slowly with H2O and aqueous alkali. If its IR has no OH bands (-3000 cm" ) then purify by redistillation. If OH bands are present then dilute with dry Et20 and shake (carefully) with aqueous NaHC03 until effervescence ceases, then wash with H2O and dry (MgSOa), filter, evaporate and distil the residue under slight vacuum then at atmospheric pressure in a N2 atmosphere. IT IS A POWERFUL ALKYLATING AGENT, AND THE FUMES ARE VERY TOXIC - CARRY ALL OPERATIONS IN AN EFFICIENT FUME CUPBOARD. [Gramstad and Hazeldine J Chem Soc 173 7956 Howells and McCown Chem Rev 77 69 1977.]... 

In some procedures, thioacetal cleavage occurs after alkylation at the sulfur atom with a reactive alkylating reagent such as methyl iodide, tnalkyloxonium tetrafluoroborate (Meerwein salt), or ethyl trifluoromethanesulfonate to give a tnalkylsulfonium salt. 

The oligomer formation during the polymerization of oxetanes has been reininves-tigated by two groups recently. Drey fuss and Dreyfuss (21) found that with oxonium salts or with ethyl trifluoromethanesulfonate as initiator, oxetane forms not only cyclic tetramer and polymer as reported by Rose, but also cyclic trimer. The amount and type of oligomer obtained depends on counter ion, temperature and solvent. Polymeri-... 

Methyl and ethyl trifluoromethanesulfonates were used to alkylate dimethyl tellurium9,10. When a compound with two organotelluro groups linked by a chain of methylene groups is treated with methyliodide in acetone, both tellurium atoms are methylated11. 

Trifluoromethanesulfonate derivatives such as 2-(2,3-naphthalimido)ethyl trifluoromethanesulfonate (NE-OTf) and 2-(2,3-antrathenedicarboxyimide)ethyl trifluoromethanesulfonate (AE-OTf) can be used for LC determination of carboxylic acids. Thermolabile carboxylic acids in mouse brain are determined by NE-OTf with the detection Emits of hundreds of femtomoles by UV detection, and a few femtomoles by FL detection. 

Fig. 4 Derivatization of PGD2 with 2-(2,3--naphthalimino)ethyl trifluoromethanesulfonate (NE-OTf) for fluorescence and mass spectrometric detection.

We sought confirmation of this suggestion by preparing poly(3-chlorothietane) directly from 3-chlorothietane monomer. This was accomplished by cationic polymerization at 0 C in bulk, with ethyl trifluoromethanesulfonate proving to be the most useful initiator. 

Block polymers using blocks other than PROZO chain were prepared. As a typical example, polytetrahydrofuran (PTHF) was introduced to AB-type and BAB-type block copolymer as shown in Scheme 18. For the synthesis of the diblock copolymer, ethyl trifluoromethanesulfonate (EtOTf) was used as initiator, while for the triblock copolymer, anhydride of TfOH was employed, where a living CROP of THF end, an oxonium species, is involved. PTHF is a hydrophobic chain both copolymers showed very good surfactant properties, when MeOZO or EtOZO was used, as observed by the surface tension value reaching to y = 30.1-28.2. 

As a typical example of surfactant synthesis via initiator method, 2-(perfluorooctyl)ethyl trifluoromethanesulfonate (RfOTf for R X in Schemes 5 and 6) was used as initiator for CROP of ROZO, then the product polymer was a very efficient surfactant, showing the lowest y value of 23.9dyncm" (R=Et, DP = 5.7) due to the specific fluor-oalkyl group hydrophilicity. ... 

---