- A Mild and Convenient Method for Tritium Labelling of Activated Aromatic Compounds Using BF3-Et2O and Tritiated Water
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A procedure for tritium exchange labelling of activated aromatic compounds using 3H2O and BF3-Et2O has been developed to prepare two radio-labelled photoprobes that are difficult to obtain by conventional methods; the applicability of the metho
- McGeady, Paul,Croteau, Rodney
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- Synthesis of 4-substituted-1,2-dihydroquinolines by means of gold-catalyzed intramolecular hydroarylation reaction of n-ethoxycarbonyl-n-propargylanilines
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An alternative Au(I)-catalyzed synthetic route to functionalized 1,2-dihydroquinolines is reported. This novel approach is based on the use of N-ethoxycarbonyl protected-Npropargylanilines as building blocks that rapidly undergo the IMHA reaction affording the 6-endo cyclization product in good to high yields. In the presence of N-ethoxycarbonyl-N-propargyl-metasubstituted anilines, the regiodivergent cyclization at the ortho-/para-position is achieved by the means of catalyst fine tuning.
- Arcadi, Antonio,Calcaterra, Andrea,Fabrizi, Giancarlo,Fochetti, Andrea,Goggiamani, Antonella,Iazzetti, Antonia,Marrone, Federico,Marsicano, Vincenzo,Mazzoccanti, Giulia,Serraiocco, Andrea
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supporting information
(2021/06/21)
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- Copper-catalyzed carbonylation of anilines by diisopropyl azodicarboxylate for the synthesis of carbamates
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A Cu-catalyzed efficient methodology for the direct carbonylation of anilines has been developed. The N-H bond cleavage and N-C bond formation were notably achieved under solvent-free conditions and a variety of carbamates were synthesized from readily available anilines using diisopropyl azodicarboxylate (DIAD) as the carbonylating source.
- Usman, Muhammad,Ren, Zhi-Hui,Wang, Yao-Yu,Guan, Zheng-Hui
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p. 107542 - 107546
(2016/11/29)
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- An efficient one-pot synthesis of: N, N ′-disubstituted ureas and carbamates from N -acylbenzotriazoles
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A facile and high-yielding one-pot synthesis of carbamates and N,N′-disubstituted symmetrical ureas from N-acylbenzotriazoles has been devised. It is believed that, the intermediate acyl-azide undergo Curtius rearrangement and in different solvents gives different products i.e. carbamates in alcohols and N,N′-disubstituted symmetrical urea in THF.
- Singh, Anoop S.,Kumar, Dhananjay,Mishra, Nidhi,Tiwari, Vinod K.
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p. 84512 - 84522
(2016/10/12)
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- One-pot preparation of carbamoyl benzotriazoles and their applications in the preparation of ureas, hydrazinecarboxamides and carbamic esters
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Carbamoyl benzotriazoles were conveniently synthesized in one-pot from carboxylic acids, diphenyl phosphorazidate (DPPA) and 1H-benzotriazole (BtH). The reactivity and applications of carbamoyl benzotriazoles were also explored. Carbamoyl benzotriazoles react smoothly with amino acids, hydrazines and alcohols, thus providing facile access to the corresponding ureas, hydrazinecarboxamides and carbamic esters, respectively, in good to excellent yields.
- Mao, Hui,Liu, Huili,Tu, Yawei,Zhong, Zhiyun,Lv, Xin,Wang, Xiaoxia
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- Reaction of organozinc halides with aryl isocyanates
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Reformatsky reagent, benzylzinc bromide or alkylzinc iodides react with aryl isocyanates directly to give corresponding N-substituted carbamates under mild reaction conditions. However, the reaction of allylzinc bromide or propargylzinc bromide with aryl isocyanates produces the corresponding N-substituted amides. The reactions provide alternative methods for the synthesis of N-substituted carbamates or amides.
- Yang, Haoran,Huang, Danfeng,Wang, Ke-Hu,Xu, Changming,Niu, Teng,Hu, Yulai
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supporting information
p. 2588 - 2593
(2013/03/28)
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- Palladium-catalyzed carbonylation of amines: Switchable approaches to carbamates and N,N′-disubstituted ureas
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Switchable access to carbamates and ureas has been developed by solvent control palladium-catalyzed carbonylation of aromatic amines under an atmosphere of carbon monoxide. A variety of N-phenylcarbamates and N,N′- diphenylureas was easily synthesized in good to excellent yields from readily available aromatic amines under mild conditions. Copyright
- Guan, Zheng-Hui,Lei, Hao,Chen, Ming,Ren, Zhi-Hui,Bai, Yinjuan,Wang, Yao-Yu
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supporting information; experimental part
p. 489 - 496
(2012/04/04)
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- Design and synthesis of novel stiripentol analogues as potential anticonvulsants
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A series of stiripentol (STP) analogues namely, 2-[(1E)-1-(1,3-benzodioxol- 5-yl)-4,4-dimethylpent-1-en-3-ylidene]-N-(aryl/H)hydrazinecarboxamides 7a-h, (±)-(5RS)-N-(aryl/H)-(1,3-benzodioxol-5-yl)-3-tert-butyl-4, 5-dihydro-1H-pyrazole-1-carboxamides (±)-8a-h, and (±)-[(5RS)-(1, 3-benzodioxol-5-yl)-3-tert-butyl-4,5-dihydro-1H-pyrazol-1-yl](aryl)methanones (±)-13a-f was synthesized by adopting appropriate synthetic routes and was pharmacologically evaluated in the preliminary anticonvulsant screens. The selected bioactive new chemical entities were subjected to ED50 determination and neurotoxicity evaluation. The most active congeners are 7h in MES screen and (±)-13b in scPTZ screen which displayed ED50 values of 87 and 110 mg/kg, respectively, as compared to that of STP (ED 50 = 277.7 and 115 mg/kg in MES and scPTZ, respectively).
- Aboul-Enein, Mohamed N.,El-Azzouny, Aida A.,Attia, Mohamed I.,Maklad, Yousreya A.,Amin, Kamilia M.,Abdel-Rehim, Mohamed,El-Behairy, Mohammed F.
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experimental part
p. 360 - 369
(2012/03/11)
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- Dibutyltin oxide catalyzed aminolysis of oxalate to carbamate, oxamate and derivatives of imidazolidine trione
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Catalytic aminolysis of oxalates by simple and substituted ureas has been shown to give carbamates, oxamates and derivatives of imidazolidine trione. Various substituted ureas and oxalates were screened to verify the applicability of the protocol. The rol
- Kunde, Lalita B.,Kalyani, Vishwanath S.,Gupte, Sunil P.
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experimental part
p. 402 - 407
(2010/08/06)
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- Synthesis and antibacterial activity of isothiazolyl oxazolidinones and analogous 3(2H)-isothiazolones
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The synthesis and antibacterial activity of several new 5-((3-oxoisothiazol-2(3H)-yl)methyl)-3-phenyloxazolidin-2-ones 8 and analogous 2-(4-substituted phenyl)-3(2H)-isothiazolones 3 and 4 substituted at 4 and/or 3-positions of the phenyl moiety with different groups of which some have shown to increase the antibacterial activity of both 3-aryl-2-oxazolidinones and 3(2H)-isothiazolones is described. The most active compounds were isothiazolyl oxazolidinones 8a,j with unsubstituted and 8b with 4-F substituted phenyl rings which showed activities higher than analogous 3(2H)-isothiazolones and comparable or superior to linezolid, vancomycin, and ciprofloxacin against some tested microorganisms. The change in position of F and/or the use of larger substituents gave compounds with reduced or no activity. Evaluation of cytotoxicity to mouse fibroblast (NIH/3T3) cells indicated that these compounds exhibit antibacterial activity at non-cytotoxic concentrations.
- Adibpour, Neda,Khalaj, Ali,Rajabalian, Saeed
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scheme or table
p. 19 - 24
(2010/03/24)
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- Unexpected Reaction of Oximinoacetoacetate with Amines: A Novel Synthesis of Carbamates
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The synthesis of alkyl carbamates by a solvent-free reaction of oximinoacetoacetate and amine at 130C is reported. A preliminary mechanism to this unexpected reaction is also given.
- Elghamry, Ibrahim
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experimental part
p. 3010 - 3015
(2009/12/01)
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- Substituent effect on aniline carbonylation reaction in the presence of the PdCl2/Fe/I2/Py catalytic system
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A study of the effect of substituents in the aromatic ring on the aniline carbonylation reaction in the presence of the PdCl2/Fe/I 2/Py catalytic system, where oxygen or nitrobenzene were used as oxidants, showed that the electronodonor substituents accelerate the aniline carbonylation reaction, when the reaction is conducted in the presence of oxygen. For nitrobenzene used as an oxidant in this reaction substituent was found to have no effect on the carbamate yield. The nitrobenzene reduction is the rate-determining step in the aniline carbonylation process.
- Karpinska,Baran,Skupinska
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p. 1105 - 1116
(2008/09/21)
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- A new access to quinazolines from simple anilines
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A new synthetic pathway to quinazolines is described. This new method uses hexamethylenetetramine in TFA and potassium ferricyanide in aqueous ethanolic KOH, starting from simple N-protected anilines. The method affords substituted quinazolines with high
- Chilin, Adriana,Marzaro, Giovanni,Zanatta, Samuele,Barbieri, Vera,Pastorini, Giovanni,Manzini, Paolo,Guiotto, Adriano
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p. 12351 - 12356
(2007/10/03)
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- Photocatalytic formation of a carbamate through ethanol-assisted carbonylation of p-nitrotoluene
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The nitroarene p-nitrotoluene is converted with a selectivity higher than 85% to the corresponding carbamate at room temperature and atmospheric pressure, using photoexcited particles of TiO2 as catalyst and EtOH as carbonylating species. The Royal Society of Chemistry 2005.
- Maldotti, Andrea,Amadelli, Rossano,Samiolo, Luca,Molinari, Alessandra,Penoni, Andrea,Tollari, Stefano,Cenini, Sergio
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p. 1749 - 1751
(2007/10/03)
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- Synthesis of Carbamates Using Yttria-Zirconia Based Lewis Acid Catalyst
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A variety of amines react with chloroformates in the presence of catalytic amount of yttria-zirconia based catalyst to afford the corresponding carbamates in excellent yields.
- Pandey, Rajesh K.,Dagade, Sharda P.,Dongare, Mohan K.,Kumar, Pradeep
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p. 4019 - 4027
(2007/10/03)
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- Ultrasound promoted 'one pot' conversion of nitrocompounds to carbamates
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An efficient ultrasound promoted novel direct conversion of nitro compounds to N-(tert-butoxycarbonyl) amines and N-(ethoxycarbonylamines) is achieved using Sn-NH4Cl for the first time.
- Chandrasekhar,Narsihmulu,Jagadeshwar
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p. 771 - 772
(2007/10/03)
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- Direct conversion of azides to carbamates and sulfonamides using Fe/NH4Cl: Effect of sonication
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A simple, direct and effective conversion of azides to carbamates and sulfonamides is achieved using Fe/NH4Cl in methanol. The influence of sonication and direct application in solution phase combinatorial chemistry are also studied by developing a 6x4 matrix library. (C) 2000 Elsevier Science Ltd.
- Chandrasekhar,Narsihmulu
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p. 7969 - 7972
(2007/10/03)
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- Kinetics and mechanism of the reactions of anilines with ethyl S-aryl thiocarbonates
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The reactions of anilines with ethyl S-(2,4-dinitrophenyl) thiocarbonate (DNPTC) and ethyl S-(2,4,6-trinitrophenyl) thiocarbonate (TNPTC) are subjected to a kinetic study in aqueous solution at 25.0 °C and ionic strength 0.2 (KCl). The reactions are studied by following spectrophotometrically (400 nm) the release of the corresponding substituted benzenethiolate anion. Under aniline excess, pseudo-first-order rate coefficients (k(obsd)) are found. Plots of k(obsd) VS [N] (N is the free substituted aniline) are linear and pH independent, with slope k(N). The Bronsted-type plots (log k(N) vs pK(a) of anilinium ions) are linear, with slopes β = 0.9 for DNPTC, in agreement with a stepwise mechanism where the breakdown of a tetrahedral addition intermediate (T(±)) is rate determining, and β = 0.54 for TNPTC, consistent with a concerted mechanism. Consideration of the results for aminolysis from the present work and those from previous studies leads to the following conclusions. (i) The tetrahedral intermediate possessing a 2,4-dinitrobenzenethio group is more stable than that including the 2,4,6-trinitrobenzenethio group. (ii) The tetrahedral intermediate possessing the 2,4,6-trinitrobenzenethio group has no existence beyond the limit of a vibration period (concerted mechanism). (iii) Tetrahedral intermediates possessing anilino groups are less stable than those derived from pyridines but are more stable than the tetrahedral intermediates derived from secondary alicyclic amines. (iv) Anilines are more reactive toward the carbonyl group of methyl 2,4-dinitrophenyl carbonate than toward the carbonyl of DNPTC.
- Castro, Enrique A.,Leandro, Leonardo,Millan, Pablo,Santos, Jose G.
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p. 1953 - 1957
(2007/10/03)
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- Multilevel selectivity in the mild and high-yielding chlorosilane- induced cleavage of carbamates to isocyanates
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The silane-induced cleavage of a series of N-p-tolylcarbamates and N- phenethylcarbamates to isocyanates has been investigated as a function of chlorosilane, carbamate substituent, and reaction conditions. Reaction yields were determined from the isolated ureas, which were formed by trapping the corresponding isocyanates with isobutylamine. Under room-temperature conditions, multilevel selectivity in carbamate activation has been demonstrated. This selectivity together with the generality of the methodology enhances the utility of carbamates as synthetic intermediates and protecting groups. To demonstrate the effectiveness of this selectivity, a series of biscarbamates were selectively monoactivated to isocyanates in excellent yields.
- Chong, Pek Y.,Janicki, Slawomir Z.,Petillo, Peter A.
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p. 8515 - 8521
(2007/10/03)
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- The Biodegradation of Low-molecular-weight Urethane Compounds by a Strain of Exophiala jeanselmei
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To further analyze the biodegradation of polyurethane polymers, we investigated the biodegradation of low-molecular-weight N-tolylcarbamate model compounds with structures closely resembling the urethane linkages found in polyurethanes based on tolylene-diisocyanate (TDT). Soil microflora were screened for microorganisms that were able to utilize toluene-2,4-dicarbamic acid, diethyl ester (compound 1) as the sole source of carbon, and the soil fungus Exophiala jeanselmei strain REN-11A was selected as the most effective strain. Several N-tolylcarbamate compounds were used, and it was found that REN-11A was able to degrade compound 1, as well as the related compound toluene-2,6-dicarbamic acid, diethyl ester, very efficiently. Further investigation showed that compound 1 was biodegraded to tolylene-2,4-diamine via the aromatic amine intermediates carbamic acid, (3-amino-4-methylphenyl)-, ethyl ester and carbamic acid, (5-amino-2-methylphenyl)-, ethyl ester.
- Owen, Stephen,Otani, Takahito,Masaoka, Satoshi,Ohe, Tatsuhiko
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p. 244 - 248
(2007/10/03)
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- Method for treating swine dysentery with the derivatives of the antibiotic A82810
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New polyether antibiotic A82810, its acyl and alkyl ester, acyl ester and urethane derivatives, and salts thereof, are useful antibacterial and anticoccidial agents and increase feed-utilization efficiency in animals. Methods of making A82810 by culture of Actinomodura fibrosa sp. nov. NRRL 18348 and synergistic compositions of the A82810 compounds with nicarbazin, 4,4'-dinitrocarbanilide, certain napthalenamine and benzenamine compounds and metichlorpindol are also provided.
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- Indirect electrochemical carbonylation of aromatic amines with a palladium catalyst
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Aromatic amines are converted to carbamates under very mild conditions, using carbon monoxide, palladium (II) acetate and copper (II) acetate in combination with anodic reoxidation.
- Hartstock, Frederick W.,Herrington, Deborah G.,McMahon, Launa B.
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p. 8761 - 8764
(2007/10/02)
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- Kinetics of the Mercury(II) Ion-promoted Desulfurisation of Thiocarbamates in Aqueous Solution
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In a 1percent dioxane-water solvent in the presence of Hg2+ ions thiocarbamates p-RC6H4NHC(S)OEt (R = MeO, Me, H, F) rapidly form complexes of 2 thiocarbamate: 1 Hg2+ stoichiometry.In the presence of an excess of Hg2+ ions partial conversion to the 2:2-complexes probably occurs which decompose to the corresponding carbamates (p-RC6H4NHCO2Et) and HgS.With R = NO2 the 2:2 complex is dominant even at low Hg2+ ion concentrations, and desulfurisation is then independent of 2+>.Electron-withdrawal by R favours the 2:2 complex but decreases its rate of decomposition to products.The effects of changes in the hydrogen ion concentration suggest that ionisation of N-bound protons in the complexes favours reaction.A mechanism is suggested.The kinetic behaviour is somewhat similar to that found previously for thiobenzamides, but the new results suggest the mechanism previously proposed may need revision.
- Satchell, Derek P. N.,Satchell, Rosemary S.,Wassef, Wasfy N.
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p. 1091 - 1094
(2007/10/02)
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- Halogenation Using Quatenary Ammonium Polyhaloides. IX. One-Step Syntheses of Acylureas and Carbamates from Amides by Use of Tetrabutylammonium Tribromide and DBU
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The reaction of amides with tetrabutylammonium tribromide (TBA Br3) (0.5 equiv) and DBU (one equiv) in dichloromethane at room temperature gave N-substituted acylureas in fairly good yields.In the presence of alcohols, the reaction of amides with TBA Br3 (one equiv) and DBU (two equiv) gave N-substituted carbamates.
- Fujisaki, Shizuo,Tomiyasu, Kazushi,Nishida, Akiko,Kajigaeshi, Shoji
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p. 1401 - 1403
(2007/10/02)
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- Production of urethane compounds
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A process for producing a urethane compound which comprises reacting at least one compound selected from the group consisting of a primary amine, a secondary amine and a urea compound with carbon monoxide and an organic hydroxyl compound in the presence of a catalyst system comprising: (a) at least one member selected from the group consisting of platinum group metals and compounds containing at least one platinum group element; and (b) at least one halogen-containing compound selected from the group consisting of alkali or alkaline earth metal halides, onium halides, compounds capable of forming onium halides in the reaction, oxo acids of halogen atoms and their salts, complex compounds containing halogen ions, organic halides and halogen molecules, in the presence of molecular oxygen and/or an organic nitro compound as an oxidizing agent at a temperature of from about 80° C. to about 300° C. under a pressure of from about 1 Kg/cm2 to about 500 Kg/cm2.
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- Antibiotic A80190, pharmaceutical compositions containing same and method of use
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New polyether antibiotic A80190, its acyl and alkyl ester, acyl ester and urethane derivatives, and salts thereof, are useful antibacterial and anticoccidial agents and increase feed-utilization efficiency in animals. Methods of making A80190 by culture of Actinomodura oligospora NRRL 15877 and synergistic compositions of the A80190 compounds with nicarbazin, 4,4'-dinitrocarbanilide, certain napthalenamine and benzenamine compounds and metichlorpindol are also provided.
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- An Exceptionally Mild, Catalytic Homogeneous Method for the Conversion of Amines into Carbamate Esters
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Aromatic amines react at room temperature and atmospheric pressure with carbon monoxide, oxygen, alcohols, and hydrochloric acid, with palladium chloride as the catalyst and copper(II) chloride as re-oxidant to give carbamate esters in fair to quantitative yields.
- Alper, Howard,Hartstock, Frederick W.
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p. 1141 - 1142
(2007/10/02)
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- Electrophilic Aromatic N-Substitution by Ethoxycarbonylnitrenium Ion generated from Ethyl Azidoformate in the Presence of Trifluoroacetic Acid
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Thermal reactions of ethyl azidoformate with aromatic compounds in the presence of trifluoroacetic acid (TFA) gave ethyl N-arylcarbamates.Toluene, nitrobenzene, or naphthalene was selectively attacked on the ortho- and para-positions, on the ortho- and meta-positions, or in the 1- and 2-positions, respectively.The yields were ca. twice as high as those for thermolysis ( a nitrene-azepine route) in the absence of TFA with the subsequent addition of TFA at room temperature.The positional selectivities for toluene and naphthalene were lower for the former thermolysis than for the latter.The reactivity of cyclohexane or toluene relative to benzene was greater in the latter thermolysis than the former.A Hammett plot with ρ - 1.7 was obtained for the formation of ethyl N-arylcarbamates in the former thermolysis in TFA-nitrobenzene (8:2 v/v); the value was more negative than that (-1.32) for the disappearance of substituted benzenes in the reaction with ethoxycarbonylnitrene.The results suggest that the thermolysis in the presence of TFA involves an electrophilic aromatic N-substitution by ethoxycarbonylnitrenium ion.
- Takeuchi, Hiroshi,Mastubara, Eiji
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p. 981 - 985
(2007/10/02)
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- UEBER DIE Si-N-BINDUNG. XLII. BESTIMMUNG DER AKTIVIERUNGSPARAMETER FUER DIE HYDROLYSE VON TRIMETHYLSILYLURETHANEN DES TYPS Me3Si(p-XC6H4)NCOOEt
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Hydrolysis reactions of silylurethanes Me3Si(p-XC6H4)NCOOEt with X = Cl, H or Me in aqueous buffer solutions, with pH values of 2.33, 3.80, and 9.38 and at temperatures of 20, 30, and 40 deg C were studied.The catalytic rate constants for the acid- and base-catalysed reactions and for the "non-catalysed" reaction k(H3O+), k(OH-), and k0 were evaluated from the pseudo first-order rate constants kexp, determined by UV spectroscopy.Activation parameters were obtained by means of the Arrhenius or Eyring equation from the dependence of rate constants of the temperature.From ρ values and activation parameters we assume for the acid and general base-catalysed reactions a SN2-Si mechanism with more or less clear d-participation at the silicon atom and for the OH--catalysed reaction a SN2-Si mechanism.
- Haenig, K.,Grosse-Ruyken, H.,Ruehlmann, K.
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p. 143 - 150
(2007/10/02)
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- UEBER DIE Si-N-BINDUNG. XLI. KINETISCHE UNTERSUCHUNGEN ZUR HYDROLYSE VON TRIMETHYLSILYLURETHANEN DES TYPS Me3Si(p-XC6H4)NCOOEt
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Hydrolysis reactions of silylurethanes Me3Si(p-XC6H4)NCOOEt (I) with X=Cl, H or Me in aqueous buffer solutions, with pH values from 1.94 to 10.00 were studied.The catalytic rate constants for the acid and base catalysed reactions and for the "non-catalysed" reaction k(H3O+), k(CH3COO-), k(H2PO-4), k(HPO2-4), k(NH3), k(OH-) and k0 were evaluated from the pseudo first-order rate constants kexp determined by UV spectroscopy.The Broensted coefficients for the base-catalysed reactions were obtained from the catalytic rate constants found and the known constants of dissociation K(HB+).The ρ values of the reactions could be derived from the ? constants given by Jaffe.The kinetical results obtained are interpreted mechanistically and are believed to also have model character for other nucleophilic substitution reactions with silicon compounds.
- Grosse-Ryuken, H.,Haenig, K.,Wagner, S.,Ruehlmann, K.,Schlapa, J.
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- Electrophilic Aromatic Substitution by Ethoxycarbonylnitrenium Ion. Reactions of Ethyl Azidoformate with Aromatics in the Presence of Trifluoroacetic Acid
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Electrophilic aromatic substitution by ethoxycarbonylnitrenium ion occurs in reactions of ethyl azidoformate with aromatics in the presence of trifluoroacetic acid, giving ethyl n-arylcarbamates.
- Takeuchi, Hiroshi,Koyama, Kikuhiko
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p. 226 - 228
(2007/10/02)
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- Fluorescence Quenching of N-Arylurethanes by Ketones
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Fluorescence and photo-Fries reaction of N-aryl-urethanes can be quenched by diffusion-controlled energy transfer to biacetyl, acetone and other aliphatic ketones.Quenching of the photo reaction and fluorescence obeys the Stern-Volmer Equation.The efficiency of quenching may by influenced by solvents and substituents changing the S1 energies of donors and acceptors.The identical rate constants determined by independent methods demonstrate that quenching of urethane fluorescence and photoreaction by aliphatic ketones occurs completely by singlet energy transfer.
- Stumpe, J.,Schwetlick, K.,Kuzmin, M. G.
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p. 400 - 408
(2007/10/02)
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- Process for producing an aromatic urethane
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An aromatic urethane is obtained at high yield without involving corrosion of a stainless steel reactor by interacting an aromatic nitro compound, an organic compound having at least one hydroxyl group therein and carbon monoxide in the presence of a cata
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