34091-69-5Relevant academic research and scientific papers
Efficient one-pot synthesis of 2-chloro-1,1, 1-trifluoro-2-alkenes under solvent-free conditions
Chen, Mu-Wang,Zhang, Xing-Guo,Zhong, Ping,Hu, Mao-Lin
experimental part, p. 756 - 763 (2009/09/05)
The improved one-pot Wittig reaction had been used to prepare trifluoromethyl-containing olefins under solvent-free conditions. Treatment of aldehydes with PPh3 and CF3CCl3 in the presence of K2CO3 at 100°C afforded 2-chloro-1,1,1-trifluoro-2-alkenes in g
New approach to the synthesis of trifluoromethylvinyl sulfides
Muzalevskiy,Shastin,Balenkova,Nenajdenko
, p. 1526 - 1533 (2008/09/18)
Nucleophilic substitution reaction of halogen atom in β-chloro-and β-bromo-β-trifluoromethylstyrenes by thiolates was studied. Stereo-and regioselectivity of the reaction with respect to the electronic and sterical properties of substituents in the aromat
Photochemical generation of highly destabilized vinyl cations: The effects of α- and β-trifluoromethyl versus α- and β-methyl substituents
Van Alem, Kaj,Belder, Geerte,Lodder, Gerrit,Zuilhof, Han
, p. 179 - 190 (2007/10/03)
(Chemical Equation Presented). The photochemical reactions in methanol of the vinylic halides 1-4, halostyrenes with a methyl or a trifluoromethyl substituent at the α- or β-position, have been investigated quantitatively. Next to E/Z isomerization, the reactions are formation of vinyl radicals, leading to reductive dehalogenation products, and formation of vinyl cations, leading to elimination, nucleophilic substitution, and rearrangement products. The vinyl cations are parts of tight ion pairs with halide as the counterion. The elimination products are the result of β-proton loss from the primarily generated α-CH3 and α-CF3 vinyl cations, or from the α-CH3 vinyl cation formed from the β-CH3 vinyl cation via a 1,2-phenyl shift. The β-CF 3 vinyl cation reacts with methanol yielding nucleophilic substitution products, no migration of the phenyl ring producing the α-CF3 vinyl cation occurs. The α-CF3 vinyl cation, which is the most destabilized vinyl cation generated thus far, gives a 1,2-fluorine shift in competition with proton loss. The experimentally derived order of stabilization of the vinyl cations photogenerated in this study, α-CF3 3 3 3, is corroborated by quantum chemical calculations, provided the effect of solvent is taken into account.
A novel approach to fluoro-containing alkenes
Korotchenko, Vasily N,Shastin, Alexey V,Nenajdenko, Valentine G,Balenkova, Elisabeth S
, p. 7519 - 7527 (2007/10/03)
A new and general one-pot transformation of aromatic aldehydes to fluorinated olefins containing -CH=C(Cl)CF3 or -CH=C(F)CClF2 moieties is described. Freons CCl3CF3 and CCl2FCClF2 were used as trifluoromethyl and difluoromethyl C2-building blocks respectively. A proposed mechanism for the reaction is discussed.
Synthesis of fluorine compounds using zinc complex of halothane
Takagi, Toshiyuki,Nakamoto, Makoto,Sato, Kazuyuki,Koyama, Mayumi,Ando, Akira,Kumadaki, Itsumaro
, p. 12667 - 12676 (2007/10/03)
We have reported the Grignard reaction of Halothane, 2-bromo-2-chloro-1,1,1-trifluoroethane (1), with ketones gave unexpected products, α-(1-bromo-1-chloro-2,2,2-trifluoroethyl)alcohols (4) at a low temperature. However, this reaction hardly proceeded with aldehydes. Now, we found the reaction of 1 with aldehydes in the presence of zinc gave not only products of type 4, but α-(1-chloro-2,2,2-trifluoroethyl)alcohols (3), the expected type of products, under mild conditions in good to moderate yields.
Synthesis of trifluoromethylalkenes and alkynes. Trifluoromethyl captodative olefins
Laurent,Le Drean,Selmi
, p. 3071 - 3074 (2007/10/02)
β-ethylthio-β-trifluoromethylketones 3 and aldehydes 4 are easily prepared from β-chloroolefines 5 and 6. Trifluoromethylalkynes 7 and captodative alkenes 8 are obtained by reaction of KOH on aldehydes 6 or 4.
Synthesis of 1-Aryl-3,3,3-trifluoro-1-propynes and 3,5-Diaryl-4-trifluoromethylisoxazoles
Meazza, Giovanni,Capuzzi, Luigi,Piccardi, Paolo
, p. 331 - 334 (2007/10/02)
Diaryl-substituted trifluoromethylisoxazoles 5a-i, 6a-c, and 6e-i are synthesized from aromatic nitrile oxides and various substituted 1-aryl-3,3,3-trifluoro-1-propynes.
Efficient Carbonyl Addition of Polyfluorochloroethyl, -ethylidene, and -ethenyl Units by Means of 1,1,1-Trichloro-2,2,2-trifluoroethane and Zinc
Fujita, Makoto,Hiyama, Tamejiro
, p. 4377 - 4384 (2007/10/02)
Thermally stable zinc carbenoid CF3CCl2ZnCl was prepared from 1,1,1-trichloro-2,2,2-trifluoroethane and zinc powder in N,N-dimethylformamide and was allowed to add to carbonyls of aldehydes and α-keto esters in excellent yields to give 1-substituted 2,2-d
PRACTICAL WAYS FROM ALDEHYDES TO 2-CHLORO-1,1,1-TRIFLUORO-2-ALKENES AND 2-CHLORO-1,1-DIFLUORO-1-ALKEN-3-OLS
Fujita, Makoto,Hiyama, Tamejiro
, p. 3655 - 3658 (2007/10/02)
A reagent system CF3CCl3/Zn(>2 mol)/Ac2O transformed aldehydes to 2-chloro-1,1,1-trifluoro-2-alkenes exclusively, whereas CF3CCl3/Zn(>2 mol)/AlCl3(cat.) converted aldehydes into 2-chloro-1,1-difluoro-1-alken-3-ols.
PRACTICAL AND STEREOCONTROLLED SYNTHESES OF BOTH (1R*,3S*)- AND (1R*,3R*)-3-(2-CHLORO-3,3,3-TRIFLUORO-1-PROPENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATES
Fujita, Makoto,Hiyama, Tamejiro,Kondo, Kiyosi
, p. 2139 - 2142 (2007/10/02)
The title compounds of (1R*,3S*) configuration were prepared from 3-formyl-2,2-dimethylcyclopropanecarboxylate by addition of CF3CCl2ZnCl, acetylation, and reductive β-elimination with zinc, whereas the (1R*,3R*) isomer was derived from Me2C=CHCH(OH)CCl2CF3 by diazoacetylation, Cu(II) catalyzed intramolecular cyclization, and the zinc reduction.
