1478-07-5Relevant academic research and scientific papers
Selective hydrolysis of pentafluorobenzotrichloride
Shipilov,Kolpashchikova,Igumnov
, p. 975 - 978 (2003)
Selective hydrolysis of pentafluorobenzotrichloride has been studied in the presence of a catalytic amount of iron(III) chloride. The main products are pentafluorobenzoyl chloride, pentafluorobenzoyl fluoride, and 4-chlorotetrafluorobenzoyl chloride. The two latter products are formed by hydrolysis of dichlorofluoromethylpentafluorobenzene and 4- chlorotetrafluorobenzotrichloride which result from halogen exchange between the methyl group and aromatic ring in the initial pentafluorobenzotrichloride. A probable mechanism for halogen exchange is proposed.
Reactions of Aldehydes with Cesium Fluoroxysulfate
Stavber, Stojan,Planinsek, Zdenka,Zupan, Marko
, p. 5334 - 5337 (1992)
Various aromatic and aliphatic aldehydes reacted at 35-40 deg C in CH3CN with CsSo4F giving acid fluorides in a good yield.In some cases formation of fluorohydrocarbons was also observed.Hammett correlation analysis of the transformation of various substituted benzaldehydes (p-OCH3, p-CH3, p-F, p-CF3, m-NO2) gave the reaction constant ρ+ = -0.38.Solvent polarity strongly influenced the conversion of aldehydes into acid fluorides, being in acetonitrile almost quantitative and completely halted in CH2Cl2, n-hexane, or tetrahydrofuran.The presence of nitrobenzene, often used as a radical scavenger, considerably reduced the acid fluoride formation.Based on experimental observations was concluded that the main intermediates involved in the conversion of aldehydes into acid fluorides with CsSO4F must be of a radical nature.
New method of preparation of fluoro compounds via utilisation of ammonium and phosphonium perfluorocyclobutane ylides as fluorination reagents
Pasenok, Sergej V.,De Roos, Marijn E.,Appel, Wolfgang K.
, p. 2977 - 2982 (1996)
Ammonium- and phosphoniumperfluorocyclobutane ylides (7-11), easily prepared from perfluorocyclobutene (1) and tertiary amines (2-4) or phosphines (5,6), smoothly react with primary or secondary alcohols (12-18) and carboxylic acids (19, 20) with formation of alkyl fluorides (21-26) or acyl fluorides (27, 28), respectively. A mechanism for the reaction is proposed.
Oxygen replacement by fluorine in carbonyl derivatives of perfluoroaromatic compounds and isomerization of perfluoroindan-1,3-dione to perfluoro-3-methylenephthalide under the action of HF/SbF5
Zonov, Yaroslav V.,Karpov, Victor M.,Platonov, Vyacheslav E.,Rybalova, Tatjana V.,Gatilov, Yuri V.
, p. 1574 - 1583 (2008/09/18)
When acted upon by HF/SbF5 at 95 °C, carbonyl groups of perfluorinated acetophenone (10), 3,4-dihydronaphthalen-1(2H)-one (8), 2,3-dihydronaphthalene-1,4-dione (9), benzocyclobutenone (6), benzocyclobutenedione (7) and indan-1-one (1) are converted into difluoromethylene groups to give the corresponding perfluoroaromatic products. Perfluoroindan-2-one (5), under the same conditions, is transformed to bis(perfluoroindan-2-yl) ether (21). On heating with HF/SbF5, perfluoroindan-1,3-dione (2) isomerizes into perfluoro-3-methylenephthalide (4) at 95 °C, and gives 4,5,6,7-tetrafluoro-3-trifluoromethyl-phthalide (14) at 130 °C. Compound 4 in the absence of a solvent dimerizes giving perfluorodispiro[phthalide-3,1′-cyclobutane-2′,3″-phthalide] (18), and when heated with SbF5 at 130 °C, it is converted into perfluoro-3-methylphthalide (3). When acted upon by HF/SbF5 at 95 °C, perfluorinated benzoic acid (12) and phthalic anhydride (13) give the corresponding products with trifluoromethyl groups.
Formation and reactions of carbanions from α-substituted perfluoroacyl fluorides
Chen, L. S.,Eapen, K. C.
, p. 93 - 100 (2007/10/02)
Aliphatic α-substituted perfluoroacyl fluorides are converted to hindered ketones in low to moderate yields on refluxing in acetonitrile with alkali metal fluorides.Other products identified in hydrolyzed reaction mixtures include perfluoroolefins and monohydroperfluoro compounds.A mechanism involving the formation of a carbanion intermediate is proposed.Evidence for the formation of carbanions has been obtained by carrying out the reaction in the presence of bromine and also in the presence of other substrates.
AROMATIC FLUORINE DERIVATIVES. XCVIII. HEPTAFLUOROPHENYLACETIC ACID. PRODUCTION AND SOME PROPERTIES
Bardin, V. V.,Furin, G. G.,Yakobson, G. G.
, p. 514 - 519 (2007/10/02)
A mixture of C6F5CHFCN and C6F5CF2CN is formed by the action of perchloryl fluoride on pentafluorophenylacetonirile in the presence of cesium fluoride.Hydrolysis of the second product gave the previously unknown heptafluorophenylacetic acid.This acid was also synthesized by the oxidation of perfluoroallylbenzene with potassium permanganate.The chloride, fluoride, amide, and methyl ester of heptafluorophenylacetic acid were obtained.
Process for the preparation of halogenated benzoyl fluorides
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, (2008/06/13)
A process for the preparation of a halogenated benzoyl fluoride, which comprises contacting a halogenated benzotrifluoride of the formula STR1 in which m and n independently of one another represent an integer from 0 to 5, the sum of m and n being 5, with at least one sulphur compound of the formula STR2 in which X denotes fluorine, chlorine or hydroxyl and Y represents hydroxyl, or X and Y together denote an oxygen atom linked to the sulphur atom by a double bond, at an elevated temperature, and after reaction with the halogenated benzotrifluoride, removing the sulphur compound from the reaction mixture in the form of a compound of the formula STR3 in which X has the meaning given and Hal represents fluorine or chlorine, the reaction product is further reacted with potassium fluoride at an elevated temperature and under increased pressure.
