Synthesis of perbromobenzoic acids and perbromobenzenes from aromatic carboxylic acids by permercuration and bromodemercuration

1977 ◽  
Vol 30 (2) ◽  
pp. 293 ◽  
Author(s):  
GB Deacon ◽  
GJ Farquharson
Keyword(s):  
Thermal Decomposition ◽  
Carboxylic Acids ◽  
Carboxyl Group ◽  
Benzoic Acids ◽  
Similar Treatment ◽  
Aromatic Carboxylic Acids ◽  
Effect Of Substituents

Permercuration of the benzoic acids XC6H4CO2H (X = o-Me, F, Cl, or Br; m- Me, F, Cl, Br, CF3, NO2 or OMe; or p-Me, F, Cl, Br, CF3 or NO2) and 2,6- X2C6H3CO2H (X = Me, Cl, or Br) with molten mercuric trifluoroacetate at c. 180-245° followed by bromodemercuration gave the corresponding perbromobenzoic acids XC6Br4CO2H or 2,6-X2C6Br3CO2H, together with the corresponding perbromobenzenes C6Br5X or m-X2C6Br4 which were formed owing to decarboxylation under permercuration conditions. Similar treatment of the acids XC6H4CO2H (X = o-NO2, CF3, or OMe; or p-OMe) and 2,6-F2C6H3CO2H gave only the appropriate perbromobenzenes. Possible mechanisms for permercuration induced decarboxylation are proposed on the basis of the effect of substituents on yields of perbromobenzoic acids and perbromobenzenes. Decarboxylation occurs more widely under permercuration conditions than on pyrolysis of mercuric carboxylates. Regiospecific mercuration meta to the carboxyl group and not decarboxylation occurred on thermal decomposition of mercuric p-methoxybenzoate.

Oxidative C-H Acyloxylation of Acetone with Carboxylic Acids under Iodine Catalysis

Synthesis ◽  
2020 ◽  
Author(s):  
Xiao-Yu Zhou ◽  
Xia Chen
Keyword(s):  
Carboxylic Acids ◽  
Sodium Chlorite ◽  
Benzoic Acids ◽  
Aromatic Carboxylic Acids ◽  
Substituted Benzoic Acids

Iodine catalyzed oxidative C(sp3)-H acyloxylation of acetone with carboxylic acids has been developed. The method employs an iodide as catalyst and sodium chlorite as oxidant. Substituted benzoic acids, naphthoic acids and hetero-aromatic carboxylic acids can be used, and 2-oxopropyl carboxylates are obtained with good to excellent yields.

Synthesis of Benzo-Fused Cyclic Compounds via Rhodium-Catalyzed Decarboxylative Coupling of Aromatic Carboxylic Acids with Alkynes

Synthesis ◽  
2021 ◽  
Author(s):  
Tetsuya Satoh ◽  
Yasuhito Inai ◽  
Yoshinosuke Usuki
Keyword(s):  
Carboxylic Acids ◽  
Catalyst System ◽  
Benzoic Acids ◽  
Naphthalene Derivatives ◽  
Aromatic Carboxylic Acids ◽  
Internal Alkynes ◽  
Decarboxylative Coupling ◽  
Substituted Benzoic Acids ◽  
Cyclic Compounds

AbstractThe decarboxylative coupling of diversely substituted benzoic acids with internal alkynes proceeds smoothly in the presence of a [RhCl(cod)]2/1,2,3,4-tetraphenyl-1,3-cyclopentadiene catalyst system to selectively produce highly substituted naphthalene derivatives. The catalyst system is applicable to constructing anthracene and benzo­[c]thiophene frameworks through reactions of naphthoic and thiophene-2-carboxylic acids, respectively.

Rhodium-catalyzed regiospecific C–H ortho-phenylation of benzoic acids with Cu/air as an oxidant

2017 ◽  
Vol 4 (3) ◽  
pp. 417-420 ◽  
Author(s):  
Shiguang Li ◽  
Guo-Jun Deng ◽  
Feifei Yin ◽  
Chao-Jun Li ◽  
Hang Gong
Keyword(s):  
Carboxylic Acids ◽  
Synthetic Approach ◽  
Benzoic Acids ◽  
Aromatic Carboxylic Acids

An efficient and practical synthetic approach for the regiospecific C–H ortho-phenylation of aromatic carboxylic acids in the absence of silver.

Synthesis and Characterisation of Acyl Coenzyme A Derivatives of Aromatic Carboxylic Acids

1974 ◽  
Vol 29 (9-10) ◽  
pp. 469-474 ◽  
Author(s):  
N Johns
Keyword(s):  
Carboxylic Acids ◽  
Potential Application ◽  
Benzoic Acids ◽  
Extinction Coefficients ◽  
Aromatic Carboxylic Acids ◽  
Uv Absorption Spectra ◽  
Thiol Esters ◽  
Gel Permeation ◽  
Acyl Coenzyme A ◽  
Derivatives Of

Abstract Acyl CoA derivatives of a number of cinnamic and benzoic acids have been synthesised via the appropriate acyl phenyl thiol esters. The reaction has potential application in the preparation of acyl CoA derivatives of radiolabelled aromatic carboxylic acids. UV absorption spectra have been determined for the CoA thiol esters following their purification by gel permeation chromato­ graphy. By comparison of the extinction in the the hydroxamate assay of Lipman and Tuttle, extinction coefficients for the series

scholarly journals Hydrogenation of benzoic acid derivatives over Pt/TiO2 under mild conditions

2021 ◽  
Vol 4 (1) ◽  
Author(s):  
Miao Guo ◽  
Xiangtao Kong ◽  
Chunzhi Li ◽  
Qihua Yang
Keyword(s):  
Electron Transfer ◽  
Benzoic Acid ◽  
High Efficiency ◽  
Carboxyl Groups ◽  
Carboxyl Group ◽  
Benzoic Acids ◽  
Catalyst Poisoning ◽  
Benzoic Acid Derivatives ◽  
Mild Conditions ◽  
Transfer Direction

AbstractHydrogenation of benzoic acid (BA) to cyclohexanecarboxylic acid (CCA) has important industrial and academic significance, however, the electron deficient aromatic ring and catalyst poisoning by carboxyl groups make BA hydrogenation a challenging transformation. Herein, we report that Pt/TiO2 is very effective for BA hydrogenation with, to our knowledge, a record TOF of 4490 h−1 at 80 °C and 50 bar H2, one order higher than previously reported results. Pt/TiO2 catalysts with electron-deficient and electron-enriched Pt sites are obtained by modifying the electron transfer direction between Pt and TiO2. Electron-deficient Pt sites interact with BA more strongly than electron-rich Pt sites, helping the dissociated H of the carboxyl group to participate in BA hydrogenation, thus enhancing its activity. The wide substrate scope, including bi- and tri-benzoic acids, further demonstrates the high efficiency of Pt/TiO2 for hydrogenation of BA derivatives.

Intercalated Organo-Bentonite as Efficient Biosorbent for Aromatic Carboxylic Acids from Wastewater

2021 ◽  
pp. 116443
Author(s):  
N. Bensid ◽  
R. Zerdoum ◽  
Z. Hattab ◽  
Y. Boutaleb ◽  
M. Bououdina
Keyword(s):  
Carboxylic Acids ◽  
Aromatic Carboxylic Acids

ChemInform Abstract: “Ligand-Free” Palladium-Catalyzed Direct C-H Bond Oxidative Acyloxylation of 2-Arylpyridines with Aromatic Carboxylic Acids.

ChemInform ◽  
2012 ◽  
Vol 43 (35) ◽  
pp. no-no
Author(s):  
Chao-Jun Hu ◽  
Xiao-Hong Zhang ◽  
Qiu-Ping Ding ◽  
Ting Lv ◽  
Shao-Peng Ge ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Aromatic Carboxylic Acids ◽  
Ligand Free ◽  
Palladium Catalyzed
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