Trifluoromethyl oxirane

Dimethyl-1,2-benzenediamine (384) and 2,2,3-trifluoro-3-trifluoromethyl-oxirane (385) gave 3-trifluoromethyl-2(l//)-quinoxalmone (386) (NaHCOs, CH2Cl2-Et20, 23°C, sealed, 12 h 78%) analogs similarly. 

With a-trifluoromethyl oxiranes. cr-Opening oxirane ring of the 2-benzenesulfonyl-2-trifluoromethyl-oxirane 374 by nucleophilic attack with 2-aminothiazole followed by Mannich cyclocondensation of the intermediate trifluoroketone gave the 6-trifluoromethyl-imidazo[2,l-A]thiazole 375 (Equation 168) <1995JFC83>. The same transformation was conducted with 2-isopropoxy-2-trifluoromethyl-3-phenyloxirane 376 and 2-imidazolidinethione and furnished the 2,3,5,6-tetrahydro-imidazo[2,l-A]thiazole 377 in good yield (Equation 169) <1999RJ0741>. 

Alkali metal fluorides are, in general, not much used for the ring-opening fluorination of epoxides. However, the oligomerization of trifluoro(trifluoromethyl)oxirane induced by cesium fluoride is of some importance for the preparation of fluorinated polymeric ethers 1. ... 

Using cesium fluoride in tetrahydrofuran it is possible to prepare the cesium salt of heptafluoro-propanolate (2) from trifluoro(trifluoromethyl)oxirane. ... 

PROPYLENE OXIDE (DOT) OXIRANE, TRIFLUORO-(TRIFLUOROMETHYL)- PERFLUORO(METHYLO-XIRANE) PERFLUOROPROPYLENE OXIDE PROPANE, l,2-EPOXY-l,l,2,3,3,3-HEXAFLUORO- PROPYLENE OXIDE HEXAFLUORIDE (TRIFLUORO-xMETHYL)TRIFLUOROOXIRANE TRIFLUORO-(TRIFLUOROMETHYL)OXIRANE... 

In contrast to HFPO, 2,2-bis(trifluoromethyl)oxirane (2) ring opens with oxygen, nitrogen, sulfur, and carbon nucleophiles at the less hindered carbon, yielding tertiary alcoholsWith diethylamine, for example, 2 affords an aminoalcohol in 83% yield. Oxirane 2 played an important role in the development of monomers from which to build highly transparent, yet readily alkali-soluble photoresist copolymers... 

As would be expected, 2,2-bis(trifluoromethyl)oxirane (2) is more easily attacked by electrophiles than its perfluorinated counterpart. " It readily undergoes ring opening with concentrated hydrochloric acid to give a chlorohydrin in 88% yield. 

Petrov, V.A. S3mthesis of polyfluorinated tertiary alcohols using ring opening reactions of 2,2-bis(trifluoromethyl)oxirane. Synthesis 2002, 2225. 

Heterocycles containing limited amount of fluorinated substituents (usually 1-3) can be named using trivial names or conventional nomenclature in combination with indication of the position of fluorinated substituents, for example, 2-fluoro-4-tri-fluoromethylpyridine. The situation becomes more complicated in case of poly-fluorinated and completely fluorinated heterocycles. In case of heterocycles with relatively small number of fluorinated substituents and well-defined stmctures, Greek or Latin numeral roots can be used. Names such as hexafluoropropene oxide, 2,2-bis (trifluoromethyl)oxirane, 2,2,3,3-tetrafluorooxetane, tetrakis(trifluoromethyl)furane, pentafluoropyridine, tetrafluoropyridazine, tetrafluoropyrimidine, and heptafluoro-quinoline are unambiguous and commonly accepted (see Fig. 0.1). 

The combination of the enhanced s-character of the CH-bond by ring strain together with a strong inductively electron-withdrawing substituent leads to a sufficient acidification for the deprotonation of (S)-2-(trifluoromethyl)oxirane 65 which leads to the chemically and configurationally stable lithium compoimd66 [Eq. (22)] [55]. The latter adds to carbonyl compounds in high yields and also reacts with triphenylsilyl and -stannyl chloride, and as well with methyl iodide with complete retention of stereochemistry in the product 67. 

Nitrogen Source Synthesis of Amines. KHMDS has been exploited as a nitrogen source in a few systems. For instance, the ring opening of (trifluoromethyl)oxirane with KHMDS, followed by acidic hydrolysis produced the desired amino alcohol in 61% yield without any variation in the enantiomeric purity (eq 25). ... 

Ketones.— Dioxolanes [involving use of (CFjCOjCO]." Epoxidation of Olefins with Hydrogen Peroxide [high yields ofepoxides are obtained in presence of RfCOR catalysts (Rf = R = CF, Rf = CFiCl, R = CFC1 Rf = CFQj, R = CClj]. " 3,3-Bis(trifluoromethyl)oxirans. 

Trifluoromethyl) trifluorooxirane Trifluoro (trifluoromethyl) oxirane Empirical CzFeO... 

Trifluorostibine. See Antimony trifluoride a,a,a-Trifluorotoluene. See Benzotrifluoride 1,1,1-Trifluorotrichloroethane. See 1,1,1-Trichloro-2,2,2-trifluoroethane Trifluoro (trifluoromethyl) oxirane. See 1,2-Epoxy-1,1,2,3,3,3-hexafluoropropane Trifluorovinyl chloride. See Chlorotrifluoroethylene Trifluralin CAS 1582-09-8... 

Trifluoro(trifluoromethyl)- oxirane Perfluoropropylene oxide C3pg0 428-59-1 166.021 gas -27.4 ... 

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