- Fluorine-Containing Organozinc Reagents. Part I. A Simple Synthesis of 2,2-Dichloro-3,3,3-trifluoropropanol
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The title compound 1, which can be regarded as synthetic equivalent of substituted 1,1,1-trifluoroacetone 2, is prepared by Zn-induced reductive addition of 1,1,1-trichloro-2,2,2-trifluoroethane (3) to formaldehyde (4).A brief survey of the scope of this C-C-bond formation leading to a variety of new CF3-containing synthetic building blocks is also given.
- Lang, Robert Werner
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- THE SYNTHESIS OF OPTICALLY ACTIVE BUILDING BLOCKS CARRYING AN α,α-DIHALOGENO-β,β,β-TRIFLUOROETHYL GROUP
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Optically active molecules with α,α-dihalogeno-β,β,β-trifluoroethyl groups were prepared by the microbial hydrolysis of the corresponding esters.
- Kitazume, Tomoya,Ohnogi, Takeshi,Lin, Jenq Tain
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- Direct electroreduction or use of an electrogenerated base : Two ways for the coupling of polyhalogenated compounds with aldehydes or ketones
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The electrochemical coupling of polyhalogenated compounds with carbonyl compounds is achieved in two ways. A carbanion RX(n)- is generated either by the direct electroreduction of RX(n)Cl or by deprotonation of RX(n)H. In this latter case the base Ph- is electrogenerated by reduction of iodobenzene. All electrolysis were carried out in an undivided cell fitted with a cadmium-coated cathode and an aluminium or magnesium sacrificial anode.
- Barhdadi, Rachid,Simsen, Blandine,Troupel, Michel,Nedelec, Jean-Yves
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p. 1721 - 1728
(2007/10/03)
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- Synthetic utility of HCFC-123 (2,2-dichloro-1,1,1-trifluoroethane): the reaction between HCFC-123 and aldehydes using zinc
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HCFC-123 (2,2-dichloro-1,1,1-trifluoroethane) reacted with zinc and aldehydes to afford predominantly either 1-substituted 2-chloro-3,3-difluoro-2-propen-1-ols or 1-substituted 2,2-dichloro-3,3,3-trifluoro-1-propanols.The reactions proceeded via 1,1-dichloro-2,2,2-trifluoroethylzinc chloride as an organozinc intermediate. - Keywords: 2,2-Dichloro-1,1,1-trifluoroethane; Reaction; Aldehydes; Zinc; 1,1-Dichloro-2,2,2-trifluoroethylzinc chloride
- Tamura, Masanori,Sekiya, Akira
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p. 119 - 122
(2007/10/02)
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- Electroorganic Chemistry. 130. A Novel Trifluoromethylation of Aldehydes and Ketones Promoted by an Electrogenerated Base
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A base generated by the electroreduction of 2-pyrrolidone deprotonated trifluoromethane to form a trifluoromethyl anion equivalent.In the presence of hexamethyldisilazane, this species reacted with a variety of aldehydes and ketones to afford (trifluoromethyl)-carbinols in high yield.
- Shono, Tatsuya,Ishifune, Manabu,Okada, Toshio,Kashimura, Shigenori
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- Electroreductive coupling of halofluoro compounds with aldehydes
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Electroreductive intermolecular coupling of halofluoro compounds such as 1,1,1-trichloro-2,2,2-trifluoroethane, methyl chlorodifluoroacetate, and perfluoroalkyl halides with aldehydes took place effectively in the presence of chlorotrimethylsilane and one of the coupling products, 2,2-dichloro-3,3,3-trifluoro-1-phenyl-1-propranol, was selectively convertible to a variety of compounds with using the electroreduction as a key reaction.
- Shono,Kise,Oka
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p. 6567 - 6570
(2007/10/02)
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- 1,1-DICHLORO-2,2,2-TRIFLUOROETHYL ZINC AND LITHIUM COMPOUNDS IN ASYMMETRIC SYNTHESIS
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Addition of 1,1-dichloro-2,2,2-trifluoroethyl zinc chloride 2 complexed with optically pure ligands leads to zero percentage of asymmetric induction due to too large a distance between the chiral centers involved.However, addition of 2 and of the correspo
- Solladie-Cavallo, A.,Quazzotti, S.
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p. 221 - 228
(2007/10/02)
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- A Facile Stereoselcetive Synthesis of (E)-1-Aryl-1,2,3,3,3-pentafluoropropenes and (E)-1-Aryl-2-chloro-1,3,3,3-tetrafluoropropenes
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Arenecarbaldehydes ArCHO were allowed to react with a carbenoid reagent CF3CX2Mtl (X=Cl, Mtl=ZnCl, X=F, Mtl=LI) to give the adducts ArCH(OH)CX2CF3 whose hydroxyl group was substituted by fluorine.Dehydrohalogenating of the resultant ArCHFCX2CF3 (X=Cl or F
- Kuroboshi, Manabu,Hiyama, Tamejiro
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p. 1607 - 1610
(2007/10/02)
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- Radical Cyclization of Trifluoromethyl-substituted Carbon: A Facile Preparation of Trifluoromethylated Five-membered Ring Compounds
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α-Trifluoromethyl carbon radicals, generated by the tributyltin radical, added intramolecularly to oleginic double bonds to afford the trifluoromethyl-substituted five-membered ring compounds.
- Watanabe, Yoshihiko,Yokozawa, Tsutomo,Takata, Toshikazu,Endo, Takeshi
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p. 431 - 434
(2007/10/02)
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- Efficient Carbonyl Addition of Polyfluorochloroethyl, -ethylidene, and -ethenyl Units by Means of 1,1,1-Trichloro-2,2,2-trifluoroethane and Zinc
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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
- Fujita, Makoto,Hiyama, Tamejiro
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p. 4377 - 4384
(2007/10/02)
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- PRACTICAL WAYS FROM ALDEHYDES TO 2-CHLORO-1,1,1-TRIFLUORO-2-ALKENES AND 2-CHLORO-1,1-DIFLUORO-1-ALKEN-3-OLS
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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.
- Fujita, Makoto,Hiyama, Tamejiro
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p. 3655 - 3658
(2007/10/02)
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- PbBr2/Al-Promoted Reductive Addition of 1,1,1-trichloro-2,2,2-trifluoroethane (Flon) to Aldehydes
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Introduction of CF3CCl2 unit into aldehydes with CF3CCl3 has been perfomed successfully by the action of catalytic PbBr2 and Al foils in DMF.
- Tanaka, Hideo,Yamashita, Shiro,Katayama, Yasumi,Torii, Sigeru
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p. 2043 - 2044
(2007/10/02)
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- EFFICIENT CARBON-CARBON BOND FORMATION WITH THERMALLY STABLE 1,1-DIHALO-2,2,2-TRIFLUOROETHYLZINC REAGENT
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The zinc carbenoids CF3CX2ZnX, prepared from CF3CX3 and zinc powder in dimethylformamide, were found thermally stable to add to aldehyde carbonyls in excellent yields.
- Fujita, Makoto,Morita, Tomoe,Hiyama, Tamejiro
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p. 2135 - 2138
(2007/10/02)
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