- Highly atom efficient synthesis of 2,2,4,5-tetrasubstituted 3(2H)-furanones having both hydroxyl and amino substituents
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We have developed a highly atom efficient synthesis of tetrasubstituted 3(2H)-furanones from easily accessible starting materials such as C,N-diarylaldonitrones and dibenzoylacetylene. Control experiments revealed that reaction of aldonitrones having electron-withdrawing groups on the C-aryl substituent in polar aprotic solvents exhibited high product selectivity while reaction temperature has only a negligible effect on product yield and selectivity.
- Antony, Jesna,Mathai, Sindhu,Natarajan, Rakesh,P. Musthafa, Sumi,Rappai, John P.,S. Devaky, Karakkattu
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supporting information
(2022/02/25)
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- Efficient aerial oxidation of different types of alcohols using ZnO nanoparticle–MnCO3-graphene oxide composites
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Graphene–metal nanocomposites have been found to remarkably enhance the catalytic performance of metal nanoparticle-based catalysts. In continuation of our previous report, in which highly reduced graphene oxide (HRG)-based nanocomposites were synthesized and evaluated, we present nanocomposites of graphene oxide (GRO) and ZnO nanoparticle-doped MnCO3 ([ZnO–MnCO3/(1%)GRO]) synthesized via a facile, straightforward co-precipitation technique. Interestingly, it was noticed that the incorporation of GRO in the catalytic system could noticeably improve the catalytic efficiency compared to a catalyst (ZnO–MnCO3) without GRO, for aerial oxidation of benzyl alcohol (BzOH) employing O2 as a nature-friendly oxidant under base-free conditions. The impacts of various reaction factors were thoroughly explored to optimize reaction conditions using oxidation of BzOH to benzaldehyde (BzH) as a model substrate. The catalysts were characterized using X-ray diffraction, thermogravimetric analysis, Fourier transform infrared spectroscopy, field-emission scanning electron microscopy, Energy dispersive X-ray spectroscopy (EDX), Brunauer-Emmett-Teller (BET), and Raman spectroscopy. The (1%)ZnO–MnCO3/(1%)GRO exhibited significant specific activity (67 mmol.g?1.hr?1) with full convversion of BzOH and >99% BzH selectivity within just 6 min. The catalytic efficiency of the (1%)ZnO–MnCO3/(1%)GRO nanocomposite was significantly better than the (1%)ZnO–MnCO3/(1%)HRG and (1%)ZnO–MnCO3 catalysts, presumably due to the existence of oxygen-possessing groups on the GRO surface and as well as a very high surface area that could have been instrumental in uniformly dispersing the active sites of the catalyst, i.e., ZnO–MnCO3. Under optimum circumstances, various kinds of alcohols were selectively transformed to respective carbonyls with full convertibility over the (1%)ZnO–MnCO3/(1%)GRO catalyst. Furthermore, the highly effective (1%)ZnO–MnCO3/(1%)GRO catalyst could be successfully reused and recycled over five consecutive runs with a marginal reduction in its performance and selectivity.
- Adil, Syed Farooq,Assal, Mohamed E.,Shaik, Mohammed Rafi,Kuniyil, Mufsir,Hashmi, Azhar,Khan, Mujeeb,Khan, Aslam,Tahir, Muhammad Nawaz,Al-Warthan, Abdulrahman,Siddiqui, Mohammed Rafiq H.
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- Reactions of Polyfluoroaromatic Organozinc Compounds with Oxalyl Chloride in DMF. Synthesis of Polyfluoroaromatic Aldehydes
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Abstract: The reaction of polyfluoroaromatic organozinc compounds with oxalyl chloride in DMF proceeds involving the Vilsmeier–Haack reagent with the formation of polyfluoroaromatic aldehydes as the major products. The use of CuI makes it possible to incr
- Vinogradov,Platonov
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p. 2264 - 2272
(2021/02/12)
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- Synthesis and Comparative Catalytic Study of Zirconia–MnCO3 or –Mn2O3 for the Oxidation of Benzylic Alcohols
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We report on the synthesis of the zirconia–manganese carbonate ZrOx(x %)–MnCO3 catalyst (where x=1–7) that, upon calcination at 500 °C, is converted to zirconia–manganese oxide ZrOx(x %)–Mn2O3. We also present a comparative study of the catalytic performance of the both catalysts for the oxidation of benzylic alcohol to corresponding aldehydes by using molecular oxygen as the oxidizing agent. ZrOx(x %)–MnCO3 was prepared through co-precipitation by varying the amounts of Zr(NO3)4 (w/w %) in Mn(NO3)2. The morphology, composition, and crystallinity of the as-synthesized product and the catalysts prepared upon calcination were studied by using scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, and powder X-ray diffraction. The surface areas of the catalysts [133.58 m2 g?1 for ZrOx(1 %)–MnCO3 and 17.48 m2 g?1 for ZrOx(1 %)–Mn2O3] were determined by using the Brunauer–Emmett–Teller method, and the thermal stability was assessed by using thermal gravimetric analysis. The catalyst with composition ZrOx(1 %)–MnCO3 pre-calcined at 300 °C exhibited excellent specific activity (48.00 mmolg?1 h?1) with complete conversion within approximately 5 min and catalyst cyclability up to six times without any significant loss in activity. The specific activity, turnover number and turnover frequency achieved is the highest so far (to the best of our knowledge) compared to the previously reported catalysts used for the oxidation of benzyl alcohol. The catalyst showed selectivity for aromatic alcohols over aliphatic alcohols.
- Assal, Mohamed E.,Kuniyil, Mufsir,Khan, Mujeeb,Al-Warthan, Abdulrahman,Siddiqui, Mohammed Rafiq H.,Tremel, Wolfgang,Nawaz Tahir, Muhammad,Adil, Syed Farooq
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p. 112 - 120
(2017/02/10)
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- Synthesis, Characterization, and Relative Study on the Catalytic Activity of Zinc Oxide Nanoparticles Doped MnCO3, -MnO2, and -Mn2O3 Nanocomposites for Aerial Oxidation of Alcohols
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Zinc oxide nanoparticles doped manganese carbonate catalysts [X% ZnOx-MnCO3] (where X = 0-7) were prepared via a facile and straightforward coprecipitation procedure, which upon different calcination treatments yields different manganese oxides, that is, [X% ZnOx-MnO2] and [X% ZnOx-Mn2O3]. A comparative catalytic study was conducted to evaluate the catalytic efficiency between carbonates and oxides for the selective oxidation of secondary alcohols to corresponding ketones using molecular oxygen as a green oxidizing agent without using any additives or bases. The prepared catalysts were characterized by different techniques such as SEM, EDX, XRD, TEM, TGA, BET, and FTIR spectroscopy. The 1% ZnOx-MnCO3 calcined at 300°C exhibited the best catalytic performance and possessed highest surface area, suggesting that the calcination temperature and surface area play a significant role in the alcohol oxidation. The 1% ZnOx-MnCO3 catalyst exhibited superior catalytic performance and selectivity in the aerial oxidation of 1-phenylethanol, where 100% alcohol conversion and more than 99% product selectivity were obtained in only 5 min with superior specific activity (48 mmol·g-1·h-1) and 390.6 turnover frequency (TOF). The specific activity obtained is the highest so far (to the best of our knowledge) compared to the catalysts already reported in the literatures used for the oxidation of 1-phenylethanol. It was found that ZnOx nanoparticles play an essential role in enhancing the catalytic efficiency for the selective oxidation of alcohols. The scope of the oxidation process is extended to different types of alcohols. A variety of primary, benzylic, aliphatic, allylic, and heteroaromatic alcohols were selectively oxidized into their corresponding carbonyls with 100% convertibility without overoxidation to the carboxylic acids under base-free conditions.
- Assal, Mohamed E.,Kuniyil, Mufsir,Shaik, Mohammed Rafi,Khan, Mujeeb,Al-Warthan, Abdulrahman,Siddiqui, Mohammed Rafiq H.,Adil, Syed Farooq
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- A highly reduced graphene oxide/ZrOx-MnCO3 or -Mn2O3 nanocomposite as an efficient catalyst for selective aerial oxidation of benzylic alcohols
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Highly reduced graphene oxide (HRG) nanocomposites of manganese carbonate doped with (1%) zirconia (ZrOx) nanoparticles [ZrOx(1%)-MnCO3/(X%)HRG (where X = 0-7)] were prepared employing a facile coprecipitation method in which the percentage of HRG was varied. The resulting nanocomposite was calcined at 300°C. Further calcination of the catalyst at 500°C resulted in the conversion of manganese carbonate to manganese oxide [ZrOx(1%)-Mn2O3/(X%)HRG]. The effect of the inclusion of HRG on the catalytic activity along with its comparative performance between carbonates and their respective oxides was studied for the liquid-phase selective oxidation of benzylic alcohols into corresponding aldehydes using molecular oxygen as the eco-friendly oxidizing agent without adding any external additives or bases. The influence of different parameters such as different percentages of HRG, reaction times, calcination temperatures, catalyst dosages and reaction temperatures have also been systematically studied in order to optimize the catalyst composition and reaction conditions. The inclusion of HRG as a dopant remarkably enhanced the catalytic efficiency of ZrOx-MnCO3 nanocatalysts for the aerobic oxidation of alcohols. The as-prepared catalysts were characterized by scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX), powder X-ray diffraction (XRD), thermal gravimetric analysis (TGA), Brunauer-Emmett-Teller (BET) surface area analysis, Raman spectroscopy and Fourier transform infrared spectroscopy (FT-IR). The catalyst with composition ZrOx(1%)-MnCO3/(1%)HRG obtained by calcination at 300°C exhibited excellent specific activity (60.0 mmol g-1 h-1) with 100% benzyl alcohol conversion and more than 99% product selectivity within an extremely short time (4 min). The same catalyst is employed for the oxidation of a wide range of substituted benzylic and aliphatic alcohols. The catalyst i.e. ZrOx(1%)-MnCO3/(1%)HRG calcined at 300°C yielded corresponding aldehydes with complete convertibility and selectivity in short reaction times under mild conditions whereas the as-prepared catalyst exhibited high selectivity for aromatic alcohols over aliphatic alcohols. The catalyst was recycled and reused at least five times without any obvious loss in its activity or selectivity.
- Assal, Mohamed E.,Shaik, Mohammed Rafi,Kuniyil, Mufsir,Khan, Mujeeb,Al-Warthan, Abdulrahman,Siddiqui, Mohammed Rafiq H.,Khan, Sohail M. A.,Tremel, Wolfgang,Tahir, Muhammad Nawaz,Adil, Syed Farooq
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p. 55336 - 55349
(2018/04/05)
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- Preparation method of pentafluorobenzaldehyde
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The invention relates to a preparation method of pentafluorobenzaldehyde, and belongs to the field of fine chemical product preparation. According to the preparation method, catalyst Ni-Al alloy, pentafluorobenzonitrile, and formic acid are subjected to reaction in water to prepare pentafluorobenzaldehyde. Ni-Al alloy is adopted, formic acid and water are taken as reducing agents, and pentafluorobenzaldehyde is prepared via reduction of pentafluorobenzonitrile. The preparation method is capable of realizing direction reduction of pentafluorobenzonitrile into pentafluorobenzaldehyde, so that reaction steps are reduced, generation of waste is reduced, production cost is reduced, and environmental pollution is reduced.
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Paragraph 0225-0226
(2017/06/02)
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- Synthesis of Aldehydes by Organocatalytic Formylation Reactions of Boronic Acids with Glyoxylic Acid
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Reported herein is a conceptually novel organocatalytic strategy for the formylation of boronic acids. New reactivity is engineered into the α-amino-acid-forming Petasis reaction occurring between aryl boronic acids, amines, and glyoxylic acids to prepare aldehydes. The operational simplicity of the process and its ability to generate structurally diverse and valued aryl, heteroaryl, and α,β-unsaturated aldehydes containing a wide array of functional groups, demonstrates the practical utility of the new synthetic strategy.
- Huang, He,Yu, Chenguang,Li, Xiangmin,Zhang, Yongqiang,Zhang, Yueteng,Chen, Xiaobei,Mariano, Patrick S.,Xie, Hexin,Wang, Wei
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supporting information
p. 8201 - 8205
(2017/06/30)
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- Laccase-Mediator System for Alcohol Oxidation to Carbonyls or Carboxylic Acids: Toward a Sustainable Synthesis of Profens
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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
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p. 2684 - 2689
(2016/12/23)
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- Hypervalent iodine/TEMPO-mediated oxidation in flow systems: A fast and efficient protocol for alcohol oxidation
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Hypervalent iodine(III)/TEMPO-mediated oxidation of various aliphatic, aromatic and allylic alcohols to their corresponding carbonyl compounds was successfully achieved by using microreactor technology. This method can be used as an alternative for the oxidation of various alcohols achieving excellent yields and selectivities in significantly shortened reaction times.
- Ambreen, Nida,Kumar, Ravi,Wirth, Thomas
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p. 1437 - 1442
(2013/08/23)
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- Synthesis of some fluorine-containing pyridinealdoximes of potential use for the treatment of organophosphorus nerve-agent poisoning
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Fluoroheterocyclic aldoximes were screened as therapeutic agents for the treatment of anticholinesterase poisoning. 2-Fluoropyridine-3- and -6-aldoxime, and 3-fluoropyridine-2- and -4-aldoxime, were synthesised. Attempts to obtain 3,5,6-trifluoropyridine-2,4-bis(aldoxime) and -2-aldoxime, however, proved unsuccessful. Pentafluorobenzaldoxime was prepared by oximation of pentafluorobenzaldehyde. Acid dissociation constants (pKa) and second-order rate constants (kox-) of the fluorinated pyridinealdoximes towards sarin were measured. 2,3,5,6-Tetrafluoropyridine-4- aldoxime had the best profile: its kox- approached that of the therapeutic oxime P2S (310 vs. 120 l mol-1 min-1), but its higher pKa (9.1 vs. 7.8) fell short of the target figure of 8 required for reactivation of inhibited acetylcholinesterase in vivo. N-alkylation of the fluorinated pyridine-aldoximes may reduce their pK a nearer to 8 and enhance their therapeutic potential. Crown Copyright
- Timperley, Christopher M.,Banks, R. Eric,Young, Ian M.,Haszeldine, Robert N.
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scheme or table
p. 541 - 547
(2011/09/15)
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- Imidazolium ionic liquids as solvents for cerium(IV)-mediated oxidation reactions
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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
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p. 517 - 524
(2007/10/03)
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- 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
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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.
- Zonov, Yaroslav V.,Karpov, Victor M.,Platonov, Vyacheslav E.,Rybalova, Tatjana V.,Gatilov, Yuri V.
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p. 1574 - 1583
(2008/09/18)
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- Exploitation of aldoxime esters as radical precursors in preparative and EPR spectroscopic roles
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Photolyses of aldoxime esters, containing a considerable range of alkyl groups, lead to cleavage of their N-O bonds and formation of aryliminyl and alkyl radicals. The process was found to be favoured by 4-methoxyacetophenone as a photosensitiser and by methoxy substituents in the aryl rings. 4-Nitro- and pentafluoro-substitutions of the aryl rings were, on the other hand, deleterious. The intermediate iminyl radicals, together with primary, secondary and tertiary alkyl radicals were characterised by 9 GHz EPR spectroscopy. Cyclopropyl, CF3, and CCl3 radicals were probably also formed, but were too reactive for direct EPR spectroscopic detection. Photosensitised reaction of benzophenone oxime O-nonanoyl ester produced the diphenylmethaniminoxyl, as well as the expected n-octyl and iminyl radicals. This indicated that O-C bond scission accompanied O-N scission for this ketoxime ester. At higher temperatures the C-centred radicals added to the starting oxime esters to produce alkoxyaminyl radicals that were also spectroscopically detected in some cases. No evidence for abstraction of the iminyl hydrogen by tertbutoxyl radicals was obtained. Instead, the t-BuO radicals added to the C=N double bonds of the oxime esters. Similarly, chlorine abstraction from alkylbenzohydroximoyl chlorides by trimethyltin radicals did not take place. Preparative scale experiments with oxime esters containing suitably unsaturated alkyl groups showed that good yields of cyclised products could be obtained in the presence of the photosensitiser. This process constitutes a general method by which carboxylic acids or acid chlorides can be converted into alkyl radicals and hence to cyclised derivatives.
- McCarroll, Andrew J.,Walton, John C.
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p. 2399 - 2409
(2007/10/03)
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- Functionally Substituted Organic Peroxides. XIX. Kinetics of the Reaction of Poly- and Perfluorinated Carbonyl Compounds with tert-Butyl Hydroperoxide
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The kinetics of noncatalytic reaction of fluorinated aliphatic and aromatic aldehydes, alkyl, cycloalkyl, and aryl ketones, and β-ketoesters with tert-butyl hydroperoxide were studied by IR spectroscopy.
- Chapurkin
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- Formation of radical anions on the reduction of carbonyl-containing perfluoroaromatic compounds in aqueous solution: A pulse radiolysis study
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Radical anions are formed on addition of hydrated electrons to pentafluoroacetophenone (PFA) and pentafluorobenzaldehyde (PFB) in aqueous solutions. On the other hand, addition of hydrated electrons to pentafluorobenzoic acid (PFBA) leads to rapid fluoride elimination. The spectrum of the radical anion of PFA has λmax at 300 and 440 nm with absorption coefficient at 440 nm ε440 = 2100 L mol-1 cm-1. PFA?- decays with a rate constant of (7 ± 3.0) × 103 s-1. It has a pKa = 7.5 and the spectrum of the conjugate acid has λmax at 270 and 460 nm with ε460 = 900 L mol-1 cm-1. The spectrum of the radical anion of PFB has λmax at 285 and 430 nm with ε430 = 800 L mol-1 cm-1. PFB?- decays with a rate of (4 ± 2) × 103 s-1. It has a pKa = 7.2 and the spectrum of the conjugate acid has weak absorption at 330 nm. Evidence for the formation of the radical anion was obtained from intermolecular electron transfer from the radical anions of PFA and PFB top-benzoquinone (Q), methyl viologen (MV2+), and 9,10-anthraquinone-2-sulfonate (AQS-). Strong reductants derived from reduction of 2,2-bipyridine (BpyH?) and 1,10-phenanthroline (PhenH?) can reduce both PFA and PFB. From the kinetics of these electron transfer reactions the reduction potentials of PFA and PFB have been determined to be -0.86 ± 0.1 and -0.75 ± 0.1 V vs NHE at pH 9.4. Addition of OH? radical to the aromatic ring of these fluorinated compounds led to rapid HF elimination and the formation of phenoxyl radicals, and addition of H? atoms led to the formation of cyclohexadienyl radical.
- Shoute, Lian C. T.,Mittal, Jai P.
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p. 14022 - 14027
(2007/10/03)
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- Activation of aromatics towards oxygen by oxidative or reductive photosensitization
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Drastic conditions of photoexcitation are necessary to perform a direct activation of aromatic substrates towards 3O2.Two ways are proposed to increase this reactivity.For the substrates which are not bearing an electron attracting group, activation paradoxically consists in oxidizing the substrate by redox photosensitization with a recyclable electron acceptor.The use of a supported photosensitizer increases the selectivity in aldehyde formation.For the substrates bearing an electron attracting group the activation is achieved by reducing a benzyl halide with an electron donor photosensitizer.Keywords: reductive sensitization / oxidative sensitization / alkyl aromatics activation / benzyl halides activation / ET activation / dioxygen
- Julliard, M.,Chanon, M.
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p. 242 - 246
(2007/10/02)
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- Process for nucleophilic fluoroalkylation of aldehydes
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Aryl difluoromethyl sulfone adds to alkehydes under phase transfer conditions to give novel substituted alcohols of the general formula wherein R is an aryl, cycloaliphatic, sec- or tert-aliphatic, or heterocyclic group and Ar is an aryl group. The substituted alcohols of formula I are of particular utility as intermediates in the synthesis of a variety of useful end products. For example, the products of formula I may be utilized in desulfonylation reactions, oxidation reactions and fluorination reactions.
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- Influence of Br- Concentration on (Br)+-Mediated Indirect Electrooxidation of Alcohols to the Corresponding Carbonyl Compounds
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Current efficiency for the (Br)+ (positive bromine species)-mediated indirect electrooxidation of alcohols to the corresponding carbonyl compounds decreased with increase in Br- concentration in dichloromethane and aqueous acidic solutions, while no concentration dependence was observed in an aqueous neutral solution.These facts suggested a general practical guideline for the indirect electrooxidation, i.e. low Br- concentration is favorable in an electrolytic solution of low nucleophilicity.It was also found that the kind of (Br)+ species formed anodically in the absence of the alcohols in dichloromethane celarly depended on charge(Q) passed as follows:Br3- at Q-1 (1F = 96480 C), Brn- (n>3) at 2/3-1, and Br2 at Q = 1F mol-1.Among these species, Br3- and Br2 seemed to be the weakest and strongest oxidizing agents, respectively.Lower efficiency for the direct electrooxidation in higher Br- concentration was rationalized as due to more predominant formation of Br3- and/or Brn- with smaller n values.
- Takiguchi, Tsuyoshi,Nonaka, Tsutomu
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p. 3137 - 3142
(2007/10/02)
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