Trifluoroethyl trifluoroacetate

Trifluoroethyl trifluoroacetate was purchased from Aldrich Chemical Company, Inc., and was distilled from calcium hydride prior to use. 

Diazoalkyl and Azidoalkyl Acids. - A convenient synthesis of dimethyl (diazomethyl)phosphonate involves the initial interaction of dimethyl (lithio-methyl)phosphonate and 2,2,2-trifluoroethyl trifluoroacetate, followed by further reaction with an arylsulfonyl azide. " The compounds (192) (R R = dialkyl or... 

Several important a-diazo ketones cannot be prepared via this approach however due to their base-sensitive nature. Danheiser and coworkers reported a detrifluoroacetylative diazo transfer strategy to combat this shortcoming. Deprotonation of substrate 52, followed by a trifluoroethyl trifluoroacetate (TFEA) quench furnished the trifluoroacetylated product. This undergoes facile detrifluoroacetylative diazo transfer from sulfonyl azide 54, to yield diazo ketone 53. In general they found TFEA to be superior to other trifluoroacetylating agents. 

Chemically, 2,2,2-trifluoroethanol behaves as a typical alcohol. It can be converted to trifluoroacetaldehyde [75-90-1] or trifluoroacetic acid [76-05-1] by various oxidi2iag agents such as aqueous chlorine solutions (51) or oxygen ia the preseace of a vanadium pentoxide catalyst (52). Under basic conditions, it adds to tetrafluoroethylene and acetylene to give, respectively, 1,1,2,2-tetrafluoroethyl 2/2/2 -trifluoroethyl ether [406-78-0] (53) and... 

On heating with sodium borohydride in glacial acetic acid. 5//-dibenz[/t,/ azepine (5) undergoes sequential acylation and reduction to yield 5-ethyl-5/7-dibcnz[A,/ ]azepine (8, R = Et).192 Similarly, reduction in trifluoroacetic acid produces the trifluoroethyl derivative 8 (R = CF3CH2 61% mp 69-70 C).193... 

Type iii-a The formation of (66) is found in the electrolysis of partially neutralized trifluoroacetic acid in the presence of diallylamine (78). It provides the crystalline hydrochloride of ds-3,4-bis-(2,2,2-trifluoroethyl)pyrrolidine (79) in 8% yield (Scheme 28) [101]. 

Kutsuna, S., Chen, L., Ohno, K., Tokuhashi, K., and Sekiya, A. Henry s law constants and hydrolysis rate constants of 2,2,2-trifluoroethyl acetate and methyl trifluoroacetate, Atmos. Environ., 38(5) 725-732, 2004. 

Male Fischer 344 rats were exposed by inhalation to 1% 2-chloro-1,1,1 -trifluoroethane for 2 h and then urine was collected for 24 h. Urinary metabolites identified by 19F nuclear magnetic resonance and gas chromatography/mass spectrometry were 2,2,2-trifluoroethyl glucuronide (16%), trifluoroacetic acid (14%), trifluoroacetaldehyde hydrate (26%), trifluoroacetaldehyde-urea adduct (40%) and inorganic fluoride (3%). A minor, unidentified metabolite was also detected. No covalent binding of fluorine-containing metabolites was observed in the liver and kidney from the exposed rats (Yin et al., 1995). In-vitro incubation of 2-chloro-1,1,1-trifluoroethane with rat liver microsomes and an NADPH-generating system has been shown to involve a dechlorination reaction (Salmon et al., 1981) that produced trifluoroacetaldehyde hydrate as the only metabolite (Yin et al., 1995). 

Of interest is the reaction of aryl isocyanates with NaBH4 and trifluoroacetic acid., V,A-Bis(2,2,2-trifluoroethyl)anilines are generated in good yields. ... 

Trifluoromethyl-l-oxa-2,4-diazole of 92 (Rf = CF3) is prepared by base-catalyzed condensation of 93 with trifluoroacetic anhydride in excellent yield (Scheme 12.13). The same method is applicable for the preparation of monofluor-omethyl, difluoromethyl, and 1,1-difluoroethyl compounds although their yields are low. The reaction of aminooxime 93 with 2-(trifluoroethylidene)-l,3-dithiane 95 under acid-catalyzed conditions, followed by ring-opening of the 1,3-dithiane ring and recyclization of oxadiazole ring provides 5-(2,2,2-trifluoroethyl)-l-oxa-2,4-diazole 96 in 38% yield (Scheme 12.13). °... 

DesMarteau and coworkers reported the preparation, X-ray crystal structure and chemistry of trifluo-roethyliodonium salts 391 by the reaction of fluoroalkyliodo-bis(trifluoroacetates) 389 with benzene and triflimide acid (390) (Scheme 2.113) [68,531,532], The structure of trifluoroethyl(phenyl)iodonium salt 391 (n = 1) was established by a single-crystal X-ray analysis [68], In contrast to fluoroalkyliodonium triflates 383, compounds 391 are stable to water and can be used as reagents for fluoroalkylation reactions in aqueous media. 

Trifluoroacetic acid anhydride is reacted with paracyclophane in a Friedel-Crafts acetylation. Then, the acylated paracyclophane is reacted with iodine and hypophosphoric acid in acetic acid as solvent. In this way, a trifluoroethyl[2,2]paracyclophane is obtained. 

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