863305-32-2Relevant articles and documents
Synthesis of o-Carboxyarylacrylic Acids by Room Temperature Oxidative Cleavage of Hydroxynaphthalenes and Higher Aromatics with Oxone
Parida, Keshaba Nanda,Moorthy, Jarugu Narasimha
, p. 8354 - 8360 (2015/09/01)
A simple procedure for the synthesis of a variety of o-carboxyarylacrylic acids has been developed with Oxone (2KHSO5·KHSO4·K2SO4); the oxidation reaction involves the stirring of methoxy/hydroxy-substituted naphthalenes, phenanthrenes, anthracenes, etc. with Oxone in an acetonitrile-water mixture (1:1, v/v) at rt. Mechanistically, the reaction proceeds via initial oxidation of naphthalene to o-quinone, which undergoes cleavage to the corresponding o-carboxyarylacrylic acid. The higher aromatics are found to yield carboxymethyl lactones derived from the initially formed o-carboxyarylacrylic acids.
Rhodium(I)-catalyzed regiospecific dimerization of aromatic acids: Two direct C-H bond activations in water
Gong, Hang,Zeng, Huiying,Zhou, Feng,Li, Chao-Jun
supporting information, p. 5718 - 5721 (2015/05/19)
2,2'-Diaryl acids are key building blocks for some of the most important and high-performance polymers such as polyesters and polyamides (imides), as well as structural motifs of MOFs (metal-organic frameworks) and biological compounds. In this study, a direct, regiospecific and practical dimerization of simple aromatic acids to generate 2,2'-diaryl acids has been discovered, which proceeds through two rhodium-catalyzed C-H activations in water. This reaction can be easily scaled up to gram level by using only 0.4-0.6 mol% of the rhodium catalyst. As a proof-of-concept, the natural product ellagic acid was synthesized in two steps by this method. On the double: An efficient, regiospecific, and general oxidative dimerization of simple aryl acids to generate diaryl acids was developed. The reaction involves two direct aryl C-H activations catalyzed by rhodium, uses water as the solvent, and can be easily scaled up. The natural product ellagic acid was obtained in only two steps by using this method.
Photocatalysis in dimethyl carbonate green solvent: Degradation and partial oxidation of phenanthrene on supported TiO2
Bellardita,Loddo,Mele,Panzeri,Parrino,Pibiri,Palmisano
, p. 40859 - 40864 (2015/01/08)
Dimethyl carbonate (DMC) is here proposed-for the first time-as a green organic solvent for photocatalytic synthesis. In this work, the photocatalytic partial oxidation of phenanthrene in dimethyl carbonate (DMC) by using anatase TiO2as the photocatalyst is described as paradigmatic example of a green synthetic process starting from polycyclic aromatic hydrocarbons (PAHs). For comparison, the same reaction carried out also in ethanol, 1-propanol or 2-propanol is reported. The use of DMC as the solvent allowed us to achieve 19% and 23% selectivity towards 9-fluorenone and 6H-benzo[c]chromen-6-one, respectively. The proposed approach may represent both a new green synthetic process and an environmentally friendly route to degradation of PAHs. This journal is
Reductive electrochemical formation of 6H-dibenzo[b,d]pyran-6-one and 2-benzopyran-1(1H)-one
Batanero, Belen,Barba, Fructuoso,Barba, Isidoro,Elinson, Michail N.
, p. 82 - 85 (2014/01/06)
In the present Letter several carbolactones (oxidative products) are obtained under aprotic cathodic conditions in the preparative scaled electrolysis of 1,2-quinones in a divided electrochemical cell and in the presence of oxygen. When 9,10-phenanthrenequinone is reduced 6H-dibenzo[b,d]pyran-6-one and [1,1′-biphenyl]-2,2′-dicarboxylic acid are obtained as major products. In the reduction of 1,2-naphthoquinone, 2-benzopyran-1(1H)-one, and 2-(2-carboxyethenyl)-benzoic acid were formed as main products. The proposed mechanism to explain the formation of these and other products, that involves an electron-transfer reaction to the oxygen in air, is now discussed.
Iron (III) perchlorate adsorbed on silica gel: A reagent for organic functional group transformations
Parmar, Anupama,Kumar, Harish
, p. 2301 - 2308 (2008/02/10)
Adsorption of Fe(ClO4)3(H2O)6 onto chromatographic-grade silica gel in the presence of organic solvents (S=water, acetonitrile, or lower fatty acids) produces a supported reagent, Fe(ClO4)3(S)6/SiO2. This reagent has been found to be effective for the rapid organic functional group transformations such as dimerization of alkynes, aromatic hydrocarbons, selective oxidation of thiols to disulfides, and transannular reactions in 1,5-cyclooctadienes on grinding using pestle and mortar in the solid state. Copyright Taylor & Francis Group, LLC.
Bis(trifluoroacetoxyiodo)benzene-induced activation of tert-butyl hydroperoxide for the direct oxyfunctionalization of arenes to quinones
Catir, Mustafa,Kilic, Hamdullah
, p. 2151 - 2154 (2007/10/03)
Various aromatic hydrocarbons were oxidized with bis(trifluoroacetoxyiodo) benzene (PIFA)/tert-butyl hydroperoxide system to afford the corresponding quinones. The reaction conditions and scope have been discussed in detail.
Cu(I)(2,5,8,11-tetramethyl-2,5,8,11-tetraazadodecane)+ as a catalyst for Ullmann's reaction
Rusonik, Irena,Cohen, Haim,Meyerstein, Dan
, p. 2024 - 2028 (2007/10/03)
Cu(I)L complexes catalyze the Ullmann reaction 2-BrC6H 4CO2- + H2O → 2-HOC 6H4CO2- + Br- + H + however the process is slow and undesirable yields of benzoic acid and diphenoic acid are formed. The optimal ligand, L, for this catalyst should enhance the rate of the process, probably via shifting the redox potential of the Cu(II/I) couple cathodically, inhibit the formation of the diphenoic acid, probably via steric hindrance, and of benzoic acid probably via buffering the solution at pH > 7. The results demonstrate that Cu(I)(2,5,8,11-tetramethyl- 2,5,8,11tetraazadodecane)+, i.e. Cu(I) with a ligand which fulfils these requirements, is a very good catalyst for this process with a selectivity of > 97% and high turnover numbers. The Royal Society of Chemistry 2003.
PRODUCTION OF AROMATIC CARBOXYLIC ACIDS
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Page 28, (2008/06/13)
A process for the production of an aromatic carboxylic acid comprising contacting in the presence of a catalyst, within a continuous flow reactor, one or more precursors of the aromatic carboxylic acid with an oxidant, such contact being effected with sai
Oxidation of polycyclic aromatic hydrocarbons catalyzed by iron tetrasulfophthalocyanine FePcS: Inverse isotope effects and oxygen labeling studies
Sorokin, Alexander,Meunier, Bernard
, p. 1269 - 1281 (2007/10/03)
Iron(III) tetrasulfophthalocyanine (FePcS) was shown to catalyze the oxidation of polycyclic aromatic hydrocarbons by H2O2. Benzo[a]pyrene and anthracene were converted to the corresponding quinones while biphenyl-2,2′-dicarboxylic acid was the main product of phenanthrene oxidation. The mechanism of the anthracene oxidation by H2O2 in the presence of FePcS or by KHSO5 with iron(III) mesotetrakis(3,5-disulfonatomesityl)porphyrin (FeTMPS) (see Figure 1 for catalyst structures) has been investigated in details by using kinetic isotope effects (KIEs) and 18O labeling studies. KIEs measured on the substrate consumption in the competitive oxidation of [H10] anthracene and [D10]anthracene by FePcS/H2O2 and FeTMPS/KHSO5 were essentially the same, 0.75 ± 0.02 and 0.76 ± 0.06, respectively. These inverse KIEs on the first oxidation step can be explained by the sp2-to-sp3 hybridization change during the addition of an electrophilic oxoiron complex to the sp2 carbon center of anthracene to form a σ adduct (this inverse KIE being enhanced by stronger slacking interactions between the perdeuterated substrate with the macrocyclic catalyst). Although the first oxidation step seems to be the same, different distribution of the oxidation products of anthracene and very different 18O incorporation into anthrone and anthraquinone in catalytic oxidations performed in the presence of H218O suggested that different active species should be responsible for anthracene oxidation in both catalytic systems. All the results obtained are compatible with an involvement of TMPSFeV=O (or TMPS+FeIV=O), having two redox equivalents above the iron(III) state of the metalloporphyrin precursor, while PcSFeIV=O (one redox equivalent above FeIII state of FePcS) was proposed to be the active species in the metallophthalocyanine-based system.
Iron (III) perchlorate: A novel reagent for functional group as well as ring transformations in organic synthesis
Kumar, Baldev,Parmar, Anupama,Rajpal, Anita,Kumar, Harish
, p. 593 - 595 (2007/10/03)
Oxidative dimerization of some aromatic hydrocarbons, diphenylacetylene and diphenyl amine, selective oxidation of thiols to disulfides, and transformation of 1,5-cyclooctadiene to the corresponding bicyclooctane derivatives through trans-annular reactions have been achieved using iron (III) perchlorate(ITP).
