- Deoxygenation of Nitrous Oxide and Nitro Compounds Using Bis(N-Heterocyclic Silylene)Amido Iron Complexes as Catalysts
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Herein, we report the efficient degradation of N2O with a well-defined bis(silylene)amido iron complex as catalyst. The deoxygenation of N2O using the iron silanone complex 4 as a catalyst and pinacolborane (HBpin) as a sacrificial reagent proceeds smoothly at 50 °C to form N2, H2, and (pinB)2O. Mechanistic studies suggest that the iron–silicon cooperativity is the key to this catalytic transformation, which involves N2O activation, H atom transfer, H2 release and oxygenation of the boron sites. This approach has been further developed to enable catalytic reductions of nitro compounds, producing amino-boranes with good functional-group tolerance and excellent chemoselectivity.
- Chen, Xi,Driess, Matthias,Du, Shaozhi,Mo, Zhenbo,Wang, Hao
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supporting information
(2021/12/03)
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- Synthesis method of 4-chlorobenzene cyanoguanidine
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The invention provides a synthetic method of 4-chlorobenzene cyanoguanidine. According to the method, diazonium p-chlorobenzene chloride and dicyandiamide are taken as main raw materials, and a targetcompound is synthesized by two steps. The preparation method comprises the following steps: carrying out coupling reaction on the diazonium p-chlorobenzene chloride and the dicyandiamide in the presence of sodium carbonate to obtain an intermediate 4-chlorphenyl azo cyanoguanidine; then putting the intermediate into diluted hydrochloric acid, performing heating and discharging nitrogen to obtaina crude product; and dissolving the crude product in a dilute sodium hydroxide solution, removing color by activated carbon, performing neutralizing by adding acid, carrying out suction filtration andwashing, and performing drying to obtain a final product 4-chlorobenzene cyanoguanidine. Chlorinated diazonium p-chlorobenzene needs to be prepared for immediate use and is prepared by reacting 4-chloroaniline with sodium nitrite under an acidic condition. The preparation method is simple, mild in reaction condition, free of organic solvent, simple and convenient in subsequent treatment, safe andenvironmentally friendly; and meanwhile, the obtained product is relatively good in purity and relatively high in yield, and the method is a relatively good and safe method for synthesizing the aromatic guanidino compound, namely, the 4-chlorobenzene cyanoguanidine.
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Paragraph 0011-0017
(2021/02/10)
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- Selective and Additive-Free Hydrogenation of Nitroarenes Mediated by a DMSO-Tagged Molecular Cobalt Corrole Catalyst
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We report on the first cobalt corrole that effectively mediates the homogeneous hydrogenation of structurally diverse nitroarenes to afford the corresponding amines. The given catalyst is easily assembled prior to use from 4-tert-butylbenzaldehyde and pyrrole followed by metalation of the resulting corrole macrocycle with cobalt(II) acetate. The thus-prepared complex is self-contained in that the hydrogenation protocol is free from the requirement for adding any auxiliary reagent to elicit the catalytic activity of the applied metal complex. Moreover, a containment system is not required for the assembly of the hydrogenation reaction set-up as both the autoclave and the reaction vessels are readily charged under a regular laboratory atmosphere.
- Sch?fberger, Wolfgang,Timelthaler, Daniel,Topf, Christoph
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supporting information
p. 2114 - 2120
(2021/07/22)
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- p-chloroaniline hydrochloride preparation method
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The invention provides a p-chloroaniline hydrochloride preparation method, which comprises: in the presence of an organic solvent azeotropic with water, using p-chloronitrobenzene as a starting raw material, adding anti-dehalogenation agent and an acid binding agent, sealing, introducing hydrogen gas, carrying out a hydrogenation reaction under the catalysis of a platinum-carbon catalyst at a hightemperature under a high pressure, cooling, filtering to remove the catalyst, collecting the filtrate, adding concentrated hydrochloric acid to the filtrate, carrying out thermal insulation for 0.5-2h at a temperature of 80-95 DEG C, continuously heating to achieve a boiling state, refluxing by a water separator until no water is separated, filtering, and drying to obtain p-chloroaniline hydrochloride. According to the present invention, the preparation method has characteristics of mild and controllable reaction conditions, simple operation and low cost, performs the two steps through the one-pot method, and provides the advanced preparation method for industrial production.
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Paragraph 0109-0114; 0119; 0124; 0132; 0140-0141; 0145; 0149
(2019/11/29)
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- Sustainable and Scalable Fe/ppm Pd Nanoparticle Nitro Group Reductions in Water at Room Temperature
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An operationally simple and general process for the safe and selective reduction of nitro groups utilizing ppm Pd supported on Fe nanomaterials in aqueous solution of designer surfactant TPGS-750-M has been developed and successfully carried out at a 100 mmol scale. Preferred use of KBH4 as the hydride source, at ambient temperature and pressure, lends this process suitable for a standard reaction vessel alleviating the need for specialized hydrogenation equipment. Calorimetry data parallel those expected for a classical nitro group reduction when measuring the heat of reaction (-896 to -850 kJ/mol).
- Gabriel, Christopher M.,Parmentier, Michael,Riegert, Christian,Lanz, Marian,Handa, Sachin,Lipshutz, Bruce H.,Gallou, Fabrice
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p. 247 - 252
(2017/02/26)
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- Reversible capture and release of aromatic amines by vicinal tricarbonyl compound
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In this paper, we report reversible capture and release of aromatic amines by diphenylpropanetrione (DPPT). Addition of aromatic amines to the central carbonyl group occurred readily at ambient temperature to provide the aromatic amine adducts of DPPT (DPPT-aromatic amines), which has a hemiaminal structure. On the other hand, washing a solution of DPPT-aromatic amine with diluted hydrochloric acid (HCl) enabled successful recovery of DPPT to demonstrate the reversible nature of this system.
- Yuki, Tatsuya,Yonekawa, Morio,Furusho, Yoshio,Sei, Yoshihisa,Tomita, Ikuyoshi,Endo, Takeshi
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p. 2868 - 2873
(2016/05/19)
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- Continuous-flow hydrogenation of olefins and nitrobenzenes catalyzed by platinum nanoparticles dispersed in an amphiphilic polymer
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A method for the flow hydrogenation of olefins and nitrobenzenes in a continuous-flow reactor containing platinum nanoparticles dispersed on an amphiphilic polystyrene-poly(ethylene glycol) resin (ARP-Pt) was developed. The hydrogenation of olefins and nitrobenzenes was completed within 31 seconds in the continuous-flow system containing ARP-Pt, giving the corresponding hydrogenated products in up to 99% yield with good chemoselectivity. Moreover, long-term (63-70 h) continuous-flow hydrogenation of styrene and nitrobenzene produced more than ten grams of ethylbenzene and aniline, respectively, without significant loss of catalytic activity. The flow hydrogenation system provides an efficient and practical method for the chemoselective reduction of olefins and nitrobenzenes. This journal is
- Osako, Takao,Torii, Kaoru,Tazawa, Aya,Uozumi, Yasuhiro
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p. 45760 - 45766
(2015/06/08)
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- The ortho effect on the acidic and alkaline hydrolysis of substituted formanilides
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The kinetics of formanilides hydrolysis were determined under first-order conditions in hydrochloric acid (0.01-8 M, 20-60°C) and in hydroxide solutions (0.01-3 M, 25 and 40°C). Under acidic conditions, second-order specific acid catalytic constants were used to construct Hammett plots. The ortho effect was analyzed using the Fujita-Nishioka method. In alkaline solutions, hydrolysis displayed both first- and second-order dependence in the hydroxide concentration. The specific base catalytic constants were used to construct Hammett plots. Ortho effects were evaluated for the first-order dependence on the hydroxide concentration. Formanilide hydrolyzes in acidic solutions by specific acid catalysis, and the kinetic study results were consistent with the AAC2 mechanism. Ortho substitution led to a decrease in the rates of reaction due to steric inhibition of resonance, retardation due to steric bulk, and through space interactions. The primary hydrolytic pathway in alkaline solutions was consistent with a modified BAC2 mechanism. The Hammett plots for hydrolysis of meta- and para-substituted formanilides in 0.10 M sodium hydroxide solutions did not show substituent effects; however, ortho substitution led to a decrease in rate constants proportional to the steric bulk of the substituent.
- Desai, Salil Dileep,Kirsch, Lee E.
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p. 471 - 488
(2015/06/30)
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- Synthesis, cytotoxic evaluation, and in silico studies of substituted N-alkylbromo-benzothiazoles
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In efforts to develop a new class of anticancer agents with improved efficacy and selective action, a series of N-alkylbromo-benzothiazoles were synthesized and evaluated for in vitro cytotoxic activity against various human cancer cell lines such as lung (A-549), prostate (PC-3), leukemia (THP-1), and colon (Caco-2). They were found to be highly active against prostate (PC-3) and leukemia (THP-1) cancer cells, moderately active against colon (Caco-2) cancer cells and less active against lung (A-549) cancer cells. Of the 12 compounds, two (11d, 11j) exhibit IC50 values of ≤ 1 μM against leukemia (THP-1) cancer cell lines. Compound 11l showed significant cytotoxic activity against the PC-3 (IC50 = 0.6 μM), THP-1 (IC50 = 3 μM) and Caco-2 cell lines (IC50 = 9.9 μM), respectively. Docking study of the synthesized ligand was done on epidermal growth factor receptor using ArgusLab flexible docking, to determine their observed activity. Further QSAR investigations with stepwise multiple linear regression analysis were applied to find correlation between various physicochemical parameters and anticancer activity. The QSAR results showed that anticancer activity could be modeled with descriptors. The predictive ability of models was cross-validated by observation of the low residual activity values and adjusted coefficient of variation (radj2) obtained by leave-one-out technique.
- Gill, Rupinder Kaur,Singh, Gagandeep,Sharma, Anuradha,Bedi,Saxena
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p. 4211 - 4222
(2013/09/02)
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- 1,2,3-Trimethoxypropane, a glycerol-based solvent with low toxicity: New utilization for the reduction of nitrile, nitro, ester, and acid functional groups with TMDS and a metal catalyst
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1,2,3-Trimethoxypropane (1,2,3-TMP) was prepared from glycerol in one step in good yield and selectivity by phase transfer catalysis. According to OECD guidelines, a toxicity study was realized for this compound. It revealed that 1,2,3-TMP has a low acute toxicity, no skin sensitization, no mutagenicity and no ecotoxicity in an aquatic environment. This compound was also used as a solvent for the reduction of organic functions using either aluminium hydride or 1,1,3,3-tetramethyldisiloxane (TMDS) as a benign hydride source. In particular, a new process for the reduction of nitriles to amines in 2-MeTHF and in 1,2,3-TMP was developed, using TMDS in combination with copper triflate (Cu(OTf)2).
- Sutter, Marc,Pehlivan, Leyla,Lafon, Romain,Dayoub, Wissam,Raoul, Yann,Metay, Estelle,Lemaire, Marc
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supporting information
p. 3020 - 3026
(2013/11/06)
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- A facile and efficient method for the selective deacylation of N-arylacetamides and 2-chloro-Narylacetamides catalyzed by SOCl2
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Thionyl chloride efficiently and selectively promoted the deacylation of N-arylacetamides and 2-chloro-N-arylacetamides, under anhydrous conditions, without effecting the ester group, aminosulfonyl group, or benzyloxyamide group. This method, which has been successfully applied to a variety of substrates including different N-arylacetamides and 2-chloro-N-arylacetamides, has the attractive advantages of inexpensive reagents, satisfactory selectivity, excellent yields, short reaction time, and convenient workup. This new method can probably be used to selectively deacylate between aromatic amides and alkyl amides. Springer Science+Business Media B.V. 2011.
- Wang, Gong-Bao,Wang, Lin-Fa,Li, Chao-Zhang,Sun, Jing,Zhou, Guang-Ming,Yang, Da-Cheng
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- Weak halogen bonding in solid haloanilinium halides probed directly via chlorine-35, bromine-81, and iodine-127 NMR spectroscopy
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A series of monohaloanilinium halides exhibiting weak halogen bonding (XB) has been prepared and characterized by 35Cl, 81Br, and 127I solid-state nuclear magnetic resonance (SSNMR) spectroscopy in magnetic fields of up to 21.1 T. The quadrupolar and chemical shift (CS) tensor parameters for halide ions (Cl-, Br-, I-) which act as electron density donors in the halogen bonds of these compounds are measured to provide insight into the possible relationship between halogen bonding and NMR observables. The NMR data for certain series of related compounds are strongly indicative of when such compounds pack in the same space group, thus providing practical structural information. Careful interpretation of the NMR data in the context of novel and previously available X-ray crystallographic data, and new gauge-including projector-augmented-wave density functional theory (GIPAW DFT) calculations has revealed several notable trends. When a series of related compounds pack in the same space group, it has been possible to interpret trends in the NMR data in terms of the strength of the halogen bond. For example, in isostructural series, the halide quadrupolar coupling constant was found to increase as the halogen bond weakens. In the case of a series of haloanilinium bromides, the 81Br isotropic chemical shift and CS tensor span both decrease as the bromide-halogen XB is weakened. These trends were reproduced using both GIPAW DFT and cluster-model calculations of the bromide ion magnetic shielding tensor. Such trends are particularly exciting given the well-known role that NMR has played historically in the characterization of hydrogen bonding.
- Attrell, Robert J.,Widdifield, Cory M.,Korobkov, Ilia,Bryce, David L.
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experimental part
p. 1641 - 1653
(2012/06/30)
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- Bromination and diazo-coupling of pyridinethiones; microwave assisted synthesis of isothiazolopyridine, pyridothiazine and pyridothiazepines
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Isothiazolopyridines, pyridothiazines and pyridothiazepines are important compounds that possess valuable biological activities. This paper reports on the synthesis of these compounds using both conventional chemical methods and modern microwave techniques. 3-Bromo-6-hydroxy-4-methyl-2-thioxo-2,3- dihydropyridine-3-carboxamide, 5-arylazo-6-hydroxy-4-methyl-2-thioxo-1,2- dihydropyridine-3-carboxamides, 3,5-bis-arylazo-6-hydroxy-4-methyl-2-thioxo-2,3- dihydropyridine-3-caboxamide, 4-methyl-2,3,6,7-tetrahydroisothiazolo[5,4-b]- pyridine-3,6-dione, 2,2'-(methylene-bis-(sulfanediyl))bis(4-methyl-6-oxo-1,6- dihydropyridine-3-carboxamide), 2-hydroxy-5-methyl-4H-pyrido[3,2-e][1,3]- thiazine-4,7(8H)-dione and 2-arylmethylene-8-hydroxy-6-methyl-2,3,4,5- tetrahydropyrido-[3,2-f][1,4]thiazepine-3,5-diones have been prepared from 6-hydroxy-4-methyl-2-thioxo-2,3-dihydropyridine-3-carboxamide. Some of these compounds were prepared using microwave-assisted reaction conditions, that provided higher yields in shorter times than the conventional methods.
- Youssef, Ayman M. S.,Azab, Mohamed E.,Youssef, Mohamed M.
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experimental part
p. 6930 - 6943
(2012/09/07)
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- Kinetics and mechanism of the anilinolysis of dicyclohexyl phosphinic chloride in acetonitrile
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The nucleophilic substitution reactions of dicyclohexyl phosphinic chloride [3; cHex2P(=O)Cl] with substituted anilines (XC6H 4NH2) and deuterated anilines (XC6H 4ND2) are investigated kinetically in acetonitrile at 60.0 °C. The anilinolysis rate is too slow to be rationalized by the stereoelectronic effects. The rate is contrary to expectations for the electronic influence of the two ligands and exhibits exceptionally great negative deviation from the Taft's eq. The deuterium kinetic isotope effects (DKIEs) involving deuterated anilines invariably change from primary normal (kH/kD > 1; max kH/kDt = 1.10 with X = 4-MeO) with the strongly basic anilines (X = 4-MeO, 4-Me, 3-Me) to secondary inverse (kH/kDt H/k Dt = 0.673 with X = 3-Cl) with the weakly basic anilines (X = H, 4-F, 4-Cl, 3-Cl). A concerted SN2 mechanism is proposed on the basis of both secondary inverse and primary normal DKIEs. The obtained DKIEs imply that the fraction of a frontside attack increases as the aniline becomes more basic. A hydrogen-bonded, four-center-type transition state is suggested for a frontside attack, while the trigonal bipyramidal pentacoordinate transition state is suggested for a backside attack.
- Ul Hoque, Md. Ehtesham,Lee, Hai Whang
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experimental part
p. 1997 - 2002
(2012/02/01)
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- Alternative method for the reduction of aromatic nitro to amine using TMDS-iron catalyst system
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The system 1,1,3,3-tetramethyldisiloxane (TMDS)/Fe(acac)3 is reported here as a new method to obtain amines from aromatic nitro compounds. Amines are synthetized in a straightforward step and are isolated as hydrochloride salts with good to excellent yields. This system has shown a good selectivity toward aryl-chloride, aryl-bromide, ester, carboxylic acid, and cyano groups. The reduction of alkylnitro compounds was unfortunately not possible using this method, only a mixture of mono and dialkylated amine was obtained.
- Pehlivan, Leyla,Métay, Estelle,Laval, Stéphane,Dayoub, Wissam,Demonchaux, Patrice,Mignani, Gérard,Lemaire, Marc
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experimental part
p. 1971 - 1976
(2011/04/22)
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- Studies with azinylacetonitriles: 2-Pyridylacetonitrile as a precursor to functionally substituted pyridines
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2-Pyridylacetonitrile (1) couples with aromatic diazonium salts to yield arylhydrazones 2a-c, that were shown to exist in the syn-form 2 rather than the anti-form 4. Compounds 2a,c reacted with hydroxylamine in refluxing DMF to yield the interesting 1,2,3-triazolylpyridines 6. Attempts to cyclize 2 to give the corresponding fused pyrazolopyridines 9 failed. On the other hand, compound 1 condensed with dimethylformamide dimethyl acetal to yield enaminonitrile 10 that could be converted into pyrazolylpyridine 11.
- Al-Sheikh, Mariam Abdullah,Elnagdi, Mohamed Hilmy
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experimental part
p. 4406 - 4413
(2010/04/24)
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- Concurrent primary and secondary deuterium kinetic isotope effects in anilinolysis of O-aryl methyl phosphonochloridothioates
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The nucleophilic substitution reactions of Y-O-aryl methyl phosphonochloridothioates with substituted anilines (XC6H 4NH2) and deuterated anilines (XC6H 4ND2) are investigated kinetically in acetonitrile at 55.0°C. The Hammett and Bronsted plots for substituent (X) variations in the nucleophiles are biphasic concave downwards with a break region between X = H and 4-Cl. The deuterium kinetic isotope effects (DKIEs) are primary normal (kH/kD = 1.03-1.30) for stronger nucleophiles (X = 4-MeO, 4-Me and H), and extremely large secondary inverse (kH/kD = 0.367-0.567) for weaker nucleophiles (X = 4-Cl, 3-Cl and 3-NO2). The cross-interaction constants are negative (ρXY(H) = -0.95 and ρXY(D) = -1.11) for stronger nucleophiles, while positive (ρXY(H) = +0.77 and ρXY(D) = +0.21) for weaker nucleophiles. These kinetic results indicate that the mechanism changes from a concerted process involving frontside nucleophilic attack for stronger nucleophiles to a stepwise process with a rate-limiting leaving group expulsion from the intermediate involving backside attack for weaker nucleophiles. A hydrogen-bonded, four-center-type transition state (TS) is suggested for a frontside attack, while a trigonal bipyramidal pentacoordinate TS is suggested for a backside attack. The unusually small DKIEs, as small as or equal to 0.4, for weaker nucleophiles seem to be ascribed to severe steric congestion in the TS.
- Ul Hoque, Md. Ehtesham,Guha, Arun Kanti,Kim, Chan Kyung,Lee, Bon-Su,Lee, Hai Whang
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experimental part
p. 2919 - 2925
(2011/02/28)
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- Kinetics and mechanism of the aminolysis of dimethyl and methyl phenyl phosphinic chlorides with anilines
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The reactions of dimethyl phosphinic chloride (1) and methyl phenyl phosphinic chloride (2) with X-anilines have been studied kinetically in acetonitrile at 15.0 and 55.0 °C, respectively. The deuterium kinetic isotope effects (KIEs) involving deuterated aniline nucleophiles (XC 6H4ND2) are also reported for the same reactions. The obtained KIEs for 1 are secondary inverse (kH/k D=0.703-0.899H/kD=1.62-2.10> 1). A concerted mechanism involving predominantly backside nucleophilic attack is proposed for the anilinolysis of 1. A concerted mechanism involving predominantly frontside attack via a hydrogen-bonded four-center-type transition state is proposed for the anilinolysis of 2. The degree of steric hindrance is the major factor that determines both the reactivity of the phosphinates and the direction of the nucleophilic attack on the phosphinates. Copyright
- Dey, Nilay Kumar,Hoque, Md. Ehtesham Ul,Kim, Chan Kyung,Lee, Bon-Su,Lee, Hai Whang
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experimental part
p. 425 - 430
(2010/04/30)
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- Highly chemo- and regioselective reduction of aromatic nitro compounds using the system silane/oxo-rhenium complexes
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(Chemical Equation Presented) The reduction of aromatic nitro compounds to the corresponding amines with silanes catalyzed by high valent oxo-rhenium complexes is reported. The catalytic systems PhMe2SiH/ReIO 2(PPh3)2 (5 mol %) and PhMe2SiH/ ReOCl3(PPh3)2 (5 mol %) reduced efficiently a series of aromatic nitro compounds in the presence of a wide range of functional groups such as ester, halo, amide, sulfone, lactone, and benzyl. This methodology also allowed the regioselective reduction of dinitrobenzenes to the corresponding nitroanilines and the reduction of an aromatic nitro group in presence of an aliphatic nitro group. 2009 American Chemical Society.
- De Noronha, Rita G.,Romao, Carlos C.,Fernandes, Ana C.
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supporting information; experimental part
p. 6960 - 6964
(2010/03/03)
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- A novel strategy for oligopeptide synthesis using a polymer-supported ammonium fluoride
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A novel method for the preparation of oligopeptides with a PS-ammonium fluoride in the solution phase is reported. The synthesis of lipid II pentapeptide is efficiently synthesized via a PS-ammonium fluoride without chromatographic purifications. The method reported here is very convenient to synthesize a relatively large amount of oligopeptides with abundantly available Fmoc-protected amino acids in a time efficient manner.
- Kurosu, Michio,Crick, Dean C.
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p. 5325 - 5328
(2007/10/03)
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- NUCLEOPHILIC SUBSTITUTION REACTIONS OF CUMYL CHLORIDES IN METHANOL
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Nucleophilic substitution reactions of cumyl chlorides with anilines in methanol have been investigated.Large negative ρY+ values in methanol and weak chloride common ion rate depression support a mechanism in which a preformed benzylic-type carbocation intermediate reacts with the solvent and the added nucleophile, aniline.All positive ρX (ρnuc) values observed and the estimated non-interactive point, ?Y+ = 0.72, strongly suggest that deprotonation of a mobile proton from the nucleophile occurs during the reaction.Fair linear correlation is exhibited for the plot of stability of carbocation, as expressed by the enthalpy of cation formation (AM1), and ?Y+, indicating that the thermodynamic driving force is nearly compensated for by the intrinsic barrier.
- Lee, Ikchoon,Koh, Han Joong,Hong, Sung Nam,Lee, Bon-Su
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p. 347 - 352
(2007/10/02)
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- New Methods and Reagents in Organic Synthesis. 60. A New Synthesis of Aromatic and Heteroaromatic Amines Using Diphenyl Phosphorazidate (DPPA)
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Aromatic and heteroaromatic organometallics (Grignard and lihium compounds) reacts with diphenyl phosphorazidate (DPPA) to give labile phosphinyltriazenes.A study of the conversion of phosphinyltriazenes into amines has revealed that reductive work-up with aluminum hydride gives much better results than acidic or alkaline work-up.Sequential treatment of aromatic and heteroaromatic organometallics with DPPA, followed by aluminum hydride provides a convenient new method for the preparation of aromatic and heteroaromatic amines.Keywords - organometallic; aromatic halide; Grignard compound; organolithium compound; aromatic amine; heteroaromatic amine; phosphinyltriazene; hydride reduction; diphenyl phosphorazidate
- Mori, Shigehiro,Aoyama, Toyohiko,Shioiri, Takayuki
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p. 1524 - 1530
(2007/10/02)
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- Substituted-4-oxo-1,6,7,8-tetrahydro-4H-pyrido[1,2-a]pyrimidines
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Nitrogen bridgehead compounds (pyrido-[1,2-a]-pyrimidine derivatives) which are useful intermediates in the making of known compounds of this class and which themselves possess PG-antagonist, analgesic, antiartheriosclerotic, tranquilizing and like pharmaceutical activity.
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