cas 602-94-8, Pentafluorobenzoic acid | Articles data

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On reactions of carbon disulphide induced by 'naked' fluoride part 1: Reactions with fluoroaromatics
On reaction with carbon disulphide and tetramethylammonium fluoride in dimethylformamide, pentafluorobenzonitrile undergoes nucleophilic substitution reactions, resulting eventually in trifluoromethylthio substituted polyfluorobenzonitrile. 2,4-Dinitrofluorobenzene and pentafluorobenzene undergo similar substitutions, however, the product mixtures are much more complex.
Ruediger, Stephan,Seppelt, Konrad
p. 25 - 28
(1997)
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Direct conversion of perfluoroalkanes and perfluoroarenes to perfluoro Grignard reagents
Magnesium anthracene selectively reduces C6F12 or C6F6 and CF3C6F11 or CF3C6F5 to C6F5MgF and CF3C6F4MgF, respectively.
Beck, Christopher M.,Park, You-Jung,Crabtree, Robert H.
p. 693 - 694
(1998)
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Mechanochemical Grignard Reactions with Gaseous CO2 and Sodium Methyl Carbonate**
A one-pot, three-step protocol for the preparation of Grignard reagents from organobromides in a ball mill and their subsequent reactions with gaseous carbon dioxide (CO2) or sodium methyl carbonate providing aryl and alkyl carboxylic acids in up to 82 % yield is reported. Noteworthy are the short reaction times and the significantly reduced solvent amounts [2.0 equiv. for liquid assisted grinding (LAG) conditions]. Unexpectedly, aryl bromides with methoxy substituents lead to symmetric ketones as major products.
Pfennig, Victoria S.,Villella, Romina C.,Nikodemus, Julia,Bolm, Carsten
supporting information

(2022/01/22)

Photoinduced FeCl3-Catalyzed Alkyl Aromatics Oxidation toward Degradation of Polystyrene at Room Temperature?
While polystyrene is widely used in daily life as a synthetic plastic, the subsequently selective degradation is still very challenging and highly required. Herein, we disclose a highly practical and selective reaction for the catalytically efficient oxidation of alkyl aromatics (including 1°, 2°, and 3° alkyl aromatics) to carboxylic acids. While dioxygen was used as the sole terminal oxidant, this protocol was catalyzed by the inexpensive and readily available ferric compound (FeCl3) with irradiation of visible light (blue LEDs) under only 1 atmosphere of O2 at room temperature. This system could further facilitate the selective degradation of polystyrene to benzoic acid, providing an important and practical tool to generate high-value chemical from abundant polystyrene wastes.
Zhang, Guoxiang,Zhang, Zongnan,Zeng, Rong
supporting information
p. 3225 - 3230
(2021/09/28)

Preparation method of pentafluorophenol
The invention relates to the field of organic synthesis, in particular to a preparation method of pentafluorophenol. The preparation method of pentafluorophenol comprises the steps as follows: 1) pentafluorobenzonitrile and bromoacetic ester are subjected to a coupling reaction in the presence of zinc powder, hydrolysis and decarboxylation are performed under the acid condition, and pentafluoroacetophenone is prepared; 2) pentafluoroacetophenone is subjected to a Baeyer-Villiger reaction in the presence of an oxidizing agent, and pentafluorophenol is prepared after hydrolysis. The preparationmethod of pentafluorophenol comprises simple and short operation steps and is low in production cost, high in industrial operability and suitable for large-scale industrial production.
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Paragraph 0071; 0072

(2020/07/24)

Selective oxidation method for toluene compounds
The invention discloses a selective oxidation method for toluene compounds. The method comprises the following steps: 1, putting a toluene compound represented by a formula (I) shown in the specification, a metalloporphyrin catalyst, an oxidant and a dispersing agent into a ball milling tank, sealing the ball milling tank, carrying out ball milling for 3-24 hours at room temperature and the rotating speed of 100-800 rpm, stopping ball milling once every 1-3 hours in the ball milling process, discharging gas in the ball milling tank, and after the reaction is finished, carrying out post-treatment on the reaction mixture to obtain a product benzoic acid compound represented by a formula (II) shown in the specification. Oxidation conversion of methylbenzene and derivatives thereof is achievedthrough solid-phase ball milling, the reaction mode is novel, the operation is convenient, and the energy consumption is low; an organic solvent and other auxiliaries are not needed, so that use of toxic and harmful organic reagents is effectively avoided, and the method is green and environmentally friendly; the peroxide content is low, and the safety coefficient is high; and benzoic acid and derivatives thereof have high selectivity and meet the social requirements of a green chemical process, an environmental compatibility chemical process and a biological compatibility chemical process inthe prior art.
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Paragraph 0126; 0127

(2019/12/25)

Efficient aerobic photooxygenation of aldehydes to carboxylic acids using cobalt(II) phthalocyanine sulfonate as a photosensitizer in organic-water biphasic media
The aerobic oxidation of a variety of aromatic aldehydes to the corresponding carboxylic acids by molecular oxygen in the presence of 4-carboxyl tetraphenylporphyrin (H2TCPP), methylene blue (MB), cobalt(II) phthalocyanine sulfonate (CoPcS) and FeTCPPCl as water-soluble photosensitizers in organic-water biphasic media at room temperature under either visible light or sunlight is described. The products were obtained with 25–100% conversion and 100% selectivity. This method has a wide range of applicabilities, has a straightforward workup procedure, is chemoselective and proceeds under mild reaction conditions. The resulting products were obtained in good yields in reasonable times.
Hajimohammadi, Mahdi,Ahmadi Khamesi, Zahra,Nosrati, Parisa
p. 167 - 173
(2018/10/31)

Method for synthesizing benzoic acid compound from benzyl alcohol compound by ultrasonic-assisted oxidation
The invention belongs to the field of synthesis of organic intermediates, and specifically discloses an ultrasonic-assisted synthesis method for a benzoic acid compound. The method comprises the following step: promoting air oxidation of benzyl alcohol by using diethylene glycol dimethyl ether under an ultrasonic-assisted action so as to obtain the benzoic acid compound, wherein a benzyl alcohol raw material is benzyl alcohol, or a benzoic acid derivative containing one to five substituents at different positions on the benzene ring of benzyl alcohol; and a reaction accelerator is the diethylene glycol dimethyl ether. The method provided by the invention has the advantages of easily-available raw materials, simple and convenient reaction conditions, short reaction time, greenness, energy conservation, high reaction selectivity and yield, excellent compatibility of substrate functional groups, and high application value.
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Paragraph 0164; 0165

(2018/09/29)

Heteroleptic μ-nitrido diiron complex supported by phthalocyanine and octapropylporphyrazine ligands: Formation of oxo species and their reactivity with fluorinated compounds
The synthesis and reactivity of N-bridged diiron macrocyclic complexes have been a topic of increasing interest in recent years since the observation of particular catalytic properties of these complexes. Herein, we report a preparation of a novel heteroleptic μ-nitrido diiron complex with unsubstituted phthalocyanine and octapropylporphyrazine macrocycles. This complex reacts with m-chloroperbenzoic acid to form high-valent diiron oxo species showing strong oxidizing properties. The formation and structure of the transient oxo species was investigated by cryospray collision induced dissociation MS/MS technique. Analysis of fragmentation pattern showed that the attachment of oxo moiety occurred at either iron phthalocyanine or at iron porphyrazine site with slight preference for the phthalocyanine iron site. The catalytic properties of the heteroleptic μ-nitrido diiron complex were evaluated in the oxidative transformation of hexafluorobenzene and perfluoro(allylbenzene).
Colomban, Cédric,Kudrik, Evgeny V.,Sorokin, Alexander B.
p. 345 - 353
(2017/08/02)

Method for preparing 2,3,4,5,6-pentafluorophenol
The invention discloses a method for preparing 2,3,4,5,6-pentafluorophenol. The method comprises the following step of in water, performing an oxidation reaction on 2,3,4,5,6-pentafluoro phenylboronic acid as shown in the formula (VI) and hydrogen peroxide, thereby obtaining 2,3,4,5,6-pentafluorophenol as shown in the formula (VII). According to the method, an oxidation reaction is implemented in the water, so that the method is low in cost, and environmental-friendly; and besides, the method is high in reaction yield and purity and relatively applicable to industrial production.
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(2017/08/29)

A convenient and efficient approach to polyfluorosalicylic acids and their tuberculostatic activity
We have developed the practical method for polyfluorosalicylic acids synthesis via nucleophilic ortho-mono-substitution of fluorine atom with magnesium methoxide. We have managed to increase the yield of targeted polyfluorosalicylic acids from good to quantitative. We have studied the tuberculostatic activity of polyfluorosalicylic acids. It has been found that minimum inhibitory concentration (MIC) of compounds is from 0.7 to 6.5 μg/mL depending on the structure.
Shchegol'Kov, Evgeny V.,Shchur, Irina V.,Burgart, Yanina V.,Saloutin, Victor I.,Solodnikov, Sergey Yu.,Krasnykh, Olga P.,Kravchenko, Marionella A.
p. 2455 - 2458
(2016/07/07)

KetoABNO/NOx Cocatalytic Aerobic Oxidation of Aldehydes to Carboxylic Acids and Access to α-Chiral Carboxylic Acids via Sequential Asymmetric Hydroformylation/Oxidation
A method for aerobic oxidation of aldehydes to carboxylic acids has been developed using organic nitroxyl and NOx cocatalysts. KetoABNO (9-azabicyclo[3.3.1]nonan-3-one N-oxyl) and NaNO2 were identified as the optimal nitroxyl and NOx sources, respectively. The mildness of the reaction conditions enables sequential asymmetric hydroformylation of alkenes/aerobic aldehyde oxidation to access α-chiral carboxylic acids without racemization. The scope, utility, and limitations of the oxidation method are further evaluated with a series of achiral aldehydes bearing diverse functional groups.
Miles, Kelsey C.,Abrams, M. Leigh,Landis, Clark R.,Stahl, Shannon S.
supporting information
p. 3590 - 3593
(2016/08/16)

Laccase-Mediator System for Alcohol Oxidation to Carbonyls or Carboxylic Acids: Toward a Sustainable Synthesis of Profens
By combining two green and efficient catalysts, such as the commercially available enzyme laccase from Trametes versicolor and the stable free radical 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO), the oxidation in water of some primary alcohols to the corresponding carboxylic acids or aldehydes and of selected secondary alcohols to ketones can be accomplished. The range of applicability of bio-oxidation is widened by applying the optimized protocol to the oxidation of enantiomerically pure 2-arylpropanols (profenols) into the corresponding 2-arylpropionic acids (profens), in high yields and with complete retention of configuration.
Galletti, Paola,Pori, Matteo,Funiciello, Federica,Soldati, Roberto,Ballardini, Alberto,Giacomini, Daria
p. 2684 - 2689
(2016/12/23)

Is carbon dioxide able to activate halogen/lithium exchange?
The unexpected effect of carbon dioxide on halogen-lithium exchange (HLE) reactions of selected haloarenes with tBuLi was investigated. In an aliphatic hydrocarbon solvent (pentane), the HLE does not occur at ca. -70 C but, surprisingly, pouring the mixture of reactants onto dry ice and subsequent aqueous acidic hydrolysis gave carboxylic acids resulting from the quench of the first-formed aryllithiums with carbon dioxide. This suggests that CO 2 acts as a promoter of the HLE and, subsequently, serves as an electrophile to trap the aryllithium intermediates that are generated in situ. Theoretical DFT calculations were used to develop a plausible mechanism for the reaction, which indicates that CO2 is a much weaker donor than tetrahydrofuran (THF) so the cleavage of inert tBuLi cubic tetramers into more reactive solvated dimeric species (tBuLi)2(CO2) 4 is disfavored by 42.8 kJ per mol of (tBuLi)4. It is possible that this deaggregation process occurs to some extent when a large excess of CO2 is used. Copyright
Durka, Krzysztof,Lulinski, Sergiusz,Dabrowski, Marek,Serwatowski, Janusz
p. 4562 - 4570
(2014/08/05)

TEMPO mediated oxidation of fluorinated alcohols to carboxylic acids
Fluorinated carboxylic acids (3a-f) have been prepared in good yield by oxidizing the corresponding alcohols (2a-f) in the presence of TEMPO (1) as catalyst, using oxidants like bleach and oxygen.
Ignatowska, Jolanta,Shyshkov, Oleg,Zipplies, Tilman,Hintzer, Klaus,R?schenthaler, Gerd-Volker
experimental part
p. 35 - 40
(2012/09/21)

INHIBITORS OF STEAROYL-COA DESATURASE
Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of diseases such as, for example, obesity.
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(2009/06/27)

Reaction of perfluorobenzocycloalkenes with SiO2-SbF5 and skeleton transformations of their carbonyl derivatives in SbF5 medium
The reaction of perfluorinated benzocyclobutene and tetraline with SiO 2-SbF5 led to the formation in a high yield of their mono- and further dicarbonyl derivatives. The monocarbonyl derivatives on heating with SbF5 underwent disproportionation into the corresponding perfluorobenzocycloalkenes and diketones. Both mono- and diketones in the SbF5 medium are liable to suffer skeleton rearrangements yielding five- and six-membered oxygen-containing heterocycles and/or products of the opening of the alicyclic fragment of the substrate, and from the perfluorobenzocyclobutenone compounds were also obtained with a number of carbon atoms greater than that of the initial ketone.
Zonov,Karpov,Platonov,Gatilov
p. 202 - 217
(2008/09/21)

Transformation of perfluorinated benzocycloalkenes and alkylbenzenes to their carbonyl derivatives under the action of CF3COOH/SbF5
Perfluorinated benzocycloalkenes (benzocyclobutene, indan, tetralin), alkylbenzocycloalkenes and alkylbenzenes react with CF3COOH/SbF5 at 20-50 °C giving the corresponding carbonyl derivatives.
Zonov, Yaroslav V.,Karpov, Victor M.,Platonov, Vyacheslav E.
p. 1058 - 1064
(2008/02/10)

Imidazolium ionic liquids as solvents for cerium(IV)-mediated oxidation reactions
Use of imidazolium ionic liquids as solvents for organic transformations with tetravalent cerium salts as oxidizing agents was evaluated. Good solubility was found for ammonium hexanitratocerate(IV) (ceric ammonium nitrate, CAN) and cerium(IV) triflate in 1-alkyl-3-methylimidazolium triflate ionic liquids. Oxidation of benzyl alcohol to benzaldehyde in 1-ethyl-3-methylimidazolium triflate was studied by in-situ FTIR spectroscopy and 13C NMR spectroscopy on carbon-13-labeled benzyl alcohol. Careful control of the reaction conditions is necessary because ammonium hexanitratocerate(IV) dissolved in an ionic liquid can transform benzyl alcohol not only into benzaldehyde but also into benzyl nitrate or benzoic acid. The selectivity of the reaction of cerium(IV) triflate with benzyl alcohol in dry ionic liquids depends on the degree of hydration of cerium(IV) triflate: anhydrous cerium(IV) triflate transforms benzyl alcohol into dibenzyl ether, whereas hydrated cerium(IV) triflate affords benzaldehyde as the main reaction product. Reactions of ammonium hexanitratocerate(IV) with organic substrates other than benzyl alcohol have been explored. 1,4-Hydroquinone is quantitatively transformed into 1,4-quinone. Anisole and naphthalene are nitrated. For the cerium-mediated oxidation reactions in ionic liquids, high reaction temperatures are an advantage because under these conditions smaller amounts of byproducts are formed.
Mehdi, Hasan,Bodor, Andrea,Lantos, Diana,Horvath, Istvan T.,De Vos, Dirk E.,Binnemans, Koen
p. 517 - 524
(2007/10/03)

Process for producing fluoroaromatic carboxylates
This invention describes processes for producing halomagnesium fluoroaryl carboxylates. In one such process, a fluoroaryl Grignard reagent is added to an anhydrous liquid ethereal medium pretreated with carbon dioxide.
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Page column 9

(2010/01/31)

Method for production of organic fluorine compound
A method for the production of an aromatic fluorine compound is provided which is capable of preventing the occurrence of benzoic acid fluorides during the course of a halogenation exchange reaction or allowing removal of the benzoic acid fluorides formed at all. A method for the production of an organic fluorine compound is disclosed which comprises preventing the occurrence of acid fluorides of an aromatic compound during the production of the organic fluorine compound by the reaction of an organic chlorine or bromine compound with a fluorinating agent in benzonitrile as a solvent or allowing removal of the acid fluorides formed.
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Page column 15

(2008/06/13)

Reactivity and reaction pathways of alkylalkoxybenzene radical cations. Part 2. Effects of 2-alkyl substituents on the relative importance of deprotonation over de-tert-butylation of 2-alkyl-5-tert-butyl-1,4-dimethoxybenzene radical cations
The 2-alkyl-5-tert-butyl-1,4-dimethoxybenzene radical cations 1+·a-e (2-alkyl = Me, Et, i-Pr, c-PrCH2 and PhCH2) generated in one-electron oxidauon of their parent compounds 1a-e by pentafluorobenzoyl peroxide or cerium(IV) sulfate were characterized by EPR spectrometry. The product analysis shows that under certain conditions 1+·a-e may collapse through two competitive pathways, i.e. deprotonation and de-tert-butylation. The deprotonation of 1+·a-e is further assured by EPR observations of the corresponding benzyl radical intermediates. The relative importance of the two pathways is greatly dependent on the structure of the alkyl substituents, the nature of the solvents and the reaction temperature. For deprotonation, the reactivity order is found to be c-PrCH2 >Me >PhCH2 >Et ? i-Pr. Copyright
Zhao, Cheng-Xue,Gong, Yue-Fa,He, Hai-Ying,Jiang, Xi-Kui
p. 688 - 694
(2007/10/03)

Elemental fluorine. Part 1. Synthesis of fluoroaromatic compounds
Direct fluorination of 4-fluorobenzoic acid, as a model substrate in a variety of reaction media, shows that 98% formic acid and concentrated sulfuric acid are excellent for promoting electrophilic fluorination. A high degree of fluorination may be achieved using concentrated sulfuric acid, showing that in this medium fluorine will act as a powerful electrophile.
Chambers, Richard D.,Skinner, Christopher J.,Hutchinson, John,Thomson, Julie
p. 605 - 609
(2007/10/03)

Method of producing pentafluorophenyl alkali metal salt using pentafluorobenzene in a chain ether type solvent
Disclosed is a production method of generating pentafluorophenyl alkali metal salt represented by a general formula C6 F5 M (M denotes an alkali metal ion) by reacting pentafluorobenzene represented by C6 HF5 wi
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(2008/06/13)

Cyclohexadienes from the rearrangement of O-aroyl-N-acetyl-N-(2,6-dimethylphenyl)hydroxylamines. Reaction in aqueous solution to meta- and para-substituted 2,6-dimethylacetanilides
O-Aryol-N-acetyl-N-(2,6-dimethylphenyl)hydroxylamines (aroyl = benzoyl, 3-nitrobenzoyl, and pentafluorobenzoyl) rearrange in acetonitrile to 1,5-dimethyl-5-aroyloxy-6-N-acetyliminocyclohexa-1,3-dienes that can be isolated as pure compounds.These cyclohexadienes react in aqueous solutions, producing m-aroyloxy- and m-hydroxy-2,6-dimethylacetanilides in an H+-catalysed reaction and the corresponding para products in a non-catalysed reaction.Analysis of the effect of the aroyloxy group suggests that the latter reaction involves heterolysis to a reactive, non-selective, ion pair that collapses to the para product, or reacts at this position with water.The meta products arise from the N-protonated cyclohexadiene reacting with solvent in a conjugate addition to give the meta-substituted phenol, or in an intramolecular reaction with the carbonyl group to give the rearranged ester.This latter reaction is proposed to proceed via an intermediate 1,3-dioxolan-2-ylium ion.The nucleophiles azide, phenylsulfinate and the methyl thioglycolate anion react in a bimolecular fashion to give meta-substituted 2,6-dimethylacetanilides.With phenylsulfinate this requires H+, while methyl thioglycolate anion reacts with the neutral cyclohexadiene.Azide exhibits reaction by both processes.These reactions are proposed to involve conjugate additions, either to the N-protonated cyclohexadiene, or, with better nucleophiles, directly on the neutral compound.These cyclohexadienes model intermediates that may form during the metabolism of certain carcinogenic amines.These results establish the presence of three electrophilic species capable of reacting with cellular nucleophiles - the highly reactive and non-selective cation formed in the heterolysis, the less reactive and more selective N-protonated species, and the neutral cyclohexadiene itself.The last electrophile is relatively unreactive, but can be a target of very good nucleophiles such as thiol anions.
Fishbein, James C.,McClelland, Robert A.
p. 653 - 662
(2007/10/02)

Electrophilic Fluorination Using Elemental Fluorine
Electrophilic fluorination by elemental fluorine is promoted by the use of protonic acids; formic and sulfuric acids are especially effective.
Chambers, Richard D.,Skinner, Christopher J.,Thomson, Julie,Hutchinson, John
p. 17 - 18
(2007/10/02)

Cleavage of pentafluorophenyl-phosphorus and -sulfur bonds by ethylmagnesium bromide
Tris(pentafluorophenyl) phosphine and bis (pentafluorophenyl) sulfide react with ethylmagnesium bromide to give products indicating cleavage of the pentafluorophenyl group from phosphorus and sulfur.Ethylated phosphorus and sulfur compounds as well as pentafluorophenylmagnesium bromide are the principal reaction products.Minor products from subsequent reaction the Grignard reagents and cleavage products have also been detected.
Sicree, Stephen A.,Tamborski, Christ
p. 269 - 273
(2007/10/02)

REACTION OF PERFLUORINATED METHYL- AND ALKENYLBENZENES WITH INORGANIC OXIDES IN THE PRESENCE OF ANTIMONY PENTAFLUORIDE
A study was carried out on the reaction of perfluorinated toluene, m-xylene, p-xylene, mesitylene, and m-(1-propenyl)toluene with inorganic oxides in the presence of antimony pentafluoride.Depending on the reaction conditions, polyfluorinated acids resulting from the consecutive conversion of trifluoromethyl groups into carboxylic acid groups are obtained after hydrolysis of the reaction mixtures.
Karpov, V. M.,Panteleev, I. V.,Platonov, V. E.
p. 1932 - 1938
(2007/10/02)

Process for the preparation of 2,3,5,6-tetrafluorobenzoic acid
2,3,5,6-Tetrafluorobenzoic acid is prepared by hydrogenolysis of pentafluorobenzoic acid (esters).
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(2008/06/13)

AROMATIC FLUORINE DERIVATIVES. XCVIII. HEPTAFLUOROPHENYLACETIC ACID. PRODUCTION AND SOME PROPERTIES
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.
Bardin, V. V.,Furin, G. G.,Yakobson, G. G.
p. 514 - 519
(2007/10/02)

Organolanthanoids. IV. Some Reactions of Bis(polyfluorophenyl)ytterbium Compounds
From reactions of bis(polyfluorophenyl)ytterbium compounds R2Yb (R=C6F5 or p-HC6F4) with trans-Rh(CO)Cl(PPh3)2, NiCl2(bpy) (bpy=2,2'-bipyridyl), NiCl2(PPh3)2, PtCl2(bpy), triphenyltin chloride, iodine and mercuric chloride, the polyfluorophenyl derivatives trans-RRh(CO)(PPh3)2, R2Ni(bpy), trans-(C6F5)2Ni(PPh3)2, (C6F5)2Pt(bpy), Ph3SnC6F5, C6F5I and (C6F5)2Hg have been obtained.Reduction to mercury metal accompanied formation of the last compound.Carbonation of (C6F5)2Yb in tetrahydrofuran followed by acidification yields pentafluorobenzoic acid and, surprisingly, a significant amount of 2,3,4,5-tetrafluorobenzoic acid, in which the aromatic hydrogen is substantially derived from tetrahydrofuran.Reaction of (C6F5)2Yb with pentafluorobenzoic acid followed by acidification also gives 2,3,4,5-tetrafluorobenzoic acid.Fluoride elimination is less extensive and less specific in a similar reaction of YbI2.
Deacon, Glen B.,Mackinnon, Peter I.,Tuong, Tran D.
p. 43 - 53
(2007/10/02)

ortho-Disubstituted F-Benzenes. III. Preparation of (F-Benzo)heterocyclic Compounds from F-Benzoic Acid and F-Phenol, and the Reactions of Some Intermediary F-Benzoyl- and F-Phenoxy Compounds
With the intention of achieving the selective ortho-substitution of F-benzoic acid and F-phenol via intramolecular nucleophilic cyclization, preparation of some requisite precursory F-benzoyl- and F-phenoxy compounds and their nucleophilic cyclization reactions were examined. 1,2-(F-Benz)isoxazol-3(2H)-one, 2-(p-tolyl)-1,2-(F-benz)isoxazol-3(2H)-one, 1,3-dimethyl(F-benzo)pyrimidine-2,4(1H,3H)-dione, and 1,4-(F-benz)oxazin-3(2H)-one were obtained from the respective precursory F-benzohydroxamic acid, N-(p-tolyl)-N-hydroxy-F-benzamide, N,N'-dimethyl-N-(F-benzoyl)urea, and 2-(F-phenoxy)acetohydrazide.Attempted cyclizations of 2-(F-phenoxy)acetohydroxamic acid and (F-phenoxy)acetic acid were accompanied by simultaneous ring-opening and resulted in the formation of the identical product : (2-hydroxy-F-phenoxy)acetic acid.Transamidation of ethyl F-benzoate with hydroxylamine failed to give F-benzohydroxamic acid, which was then obtained by the catalytic debenzylation of N-benzyloxy-F-benzamide.
Inukai, Yoshinari,Oono, Yoshitsugu,Sonoda, Takaaki,Kobayashi, Hiroshi
p. 3447 - 3452
(2007/10/02)