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103-82-2Relevant articles and documents
Synthesis, crystal structure of Co(II)(6-methoxybenzothiazole-2-carboxylate)2(DMF)2 and its application to carbonylation of benzyl chloride
Zhang, Bin,Li, Jianli,Chen, Wei,Wang, Yunxia,Shi, Zhen
, p. 111 - 114 (2010)
A new complex, Co(MBTC)2(DMF)2 (MBTC(6-methoxybenzothiazole-2-carboxylate, DMF=N,N-dimethylformamide), was synthesized in DMF solution and characterized by single crystal X-ray diffraction analysis. Using the cobalt complex as catalyst, phenylacetic acid was prepared by the carbonylation of benzyl chloride with carbon monoxide (0.1 MPa). The effects of solvents, phase transfer catalysts and temperature on the reactions were investigated. The yield of phenylacetic acid was higher than 90% in optimized condition.
Lanthanide-Promoted and Nickel Cyanide Catalyzed Carbonylation Reactions under Phase-Transfer Conditions
Amer, Ibrahim,Alper, Howard
, p. 927 - 930 (1989)
The nickel cyanide and phase transfer catalyzed carbonylation of benzyl chlorides is promoted by lanthanide salts .This simple reaction is sensitive to the concentration of the lanthanide compound, sodium hydroxide, quaternary ammonium salt, and nickel catalyst.The nature of the organic phase and phase transfer agent also influences the reaction rate.The acceleration of the reaction may be a consequence of coordination of a nickel cyanide nitrogen lone pair to the lanthanide salt.
Photoreactivity of 1-Pyrenylmethyl Esters. Dependence on the Structure of the Carboxylic Acid Moieties and the Nature of the Excited States
Iwamura, Michiko,Tokuda, Kazuko,Koga, Noboru,Iwamura, Hiizu
, p. 1729 - 1732 (1987)
While the photolysis of 1-pyrenylmethyl phenylacetates in methanol gave the original phenylacetic acids, irradation of the 1-naphthoate and 9-anthracenecarboxylate leads to the formation of the intramolecular exciplexes that are inert to the photolysis.The Φf and τf values of these esters have been determined.
Penicillin G amidase-catalysed hydrolysis of phenylacetic hydrazides on a solid phase: A new route to enzyme-cleavable linkers
Basso, Alessandra,Ebert, Cynthia,Gardossi, Lucia,Linda, Paolo,Phuong, Thao Tran,Zhu, Mingzhao,Wessjohann, Ludger
, p. 963 - 966 (2005)
A novel catalytic property of penicillin G amidase (PGA) is described. Unexpectedly, the enzyme can hydrolyse hydrazide bonds with good efficiency, and in solution the enzyme shows a selectivity that is similar to phenylacetamides. The hydrolysis of phenylacetic hydrazides releases hydrazine, but no inhibition due to the formation of such reactive compounds was observed. This novel catalytic property was assayed also on a solid phase as a pioneering route for the design of enzyme-cleavable linkers and masked scavengers for ketones. On a solid phase a phenylacetic hydrazide compound was chemically synthesised on PEGA1900 and PEGA+ (two co-polymers of acrylamide and ethylene glycol) and the efficiency of PGA in the release of phenylacetic acid depended on the diffusion of the protein inside the polymer. On PEGA+ the enzyme, as previously described, shows a good diffusion due to an improved electrostatic interaction with PGA thus achieving good hydrolytic conversions.
Microwave-assisted rapid hydrolysis and preparation of thioamides by Willgerodt-Kindler reaction
Matloubi Moghaddam,Ghaffarzadeh
, p. 317 - 321 (2001)
Aldehydes and aryl alkyl ketones were efficiently transformed to thioamides with the same number of carbon atoms via Willgerodt-Kindler reaction under microwave irradiation in solvent-free conditions. The thioamides obtained were hydrolyzed to corresponding carboxylic acids with microwave dielectric heating in one minute. Both reactions are very fast and the yields are excellent.
Copper-catalysed Reaction of Arylacetylenes with C,N-Diarylnitrones
Okuro, Kazumi,Enna, Masahiro,Miura, Masahiro,Nomura, Masakatsu
, p. 1107 - 1108 (1993)
Reaction of arylacetylenes with C,N-diarylnitrones is effectively catalysed by copper(I) iodide-dppe in the presence of potassium carbonate to give the corresponding 1-azabut-1-en-3-yne (iminopropyne) derivatives in good yield.
Preparation of Protein Conjugates via Homobifunctional Diselenoester Cross-Linker
Yin, Xu-Guang,Gao, Xiao-Fei,Du, Jing-Jing,Zhang, Xiao-Kang,Chen, Xiang-Zhao,Wang, Jian,Xin, Ling-Ming,Lei, Ze,Liu, Zheng,Guo, Jun
, p. 5796 - 5799 (2016)
Adipic acid diselenoester was developed as an efficient cross-linker for covalent protein conjugation with a variety of small molecular haptens, including mono- and disaccharides, peptide, fluorescence dye, and nicotine. Compared to the counterparts of N-hydroxysuccinimide (NHS) and p-nitrophenyl (PNP) linkers, the diselenoester linker demonstrates improved balance between reactivity and stability and coupling of haptens to proteins under mild conditions with high incorporation efficiency.
Permanganate Ion Oxidations. 14. Kinetics and Mechanism of the Oxidation of Aliphatic Aldehydes in Acid Media
Freeman, Fillmore,Lin, Doris K.,Moore, Gregory R.
, p. 56 - 59 (1982)
The kinetics and mechanism of the permanganate ion oxidation of 2,2-dimethylpropanal (pivalaldehyde, 4) and other aliphatic aldehydes over the pH range 2.80-6.86 have been investigated.The oxidation, which shows general-acid catalysis, is first order in and first order in ->.The mechanism of the Mn(VII) oxidation of aliphatic aldehydes is compared with that proposed for Cr(VI).
Towards the rehabilitation of the Mathews' 'dry' hydrolysis reaction using microwave technology
Chemat, Farid
, p. 5555 - 5557 (2002)
The Mathews' reaction is a one-pot preparation of carboxylic acids from their corresponding nitriles or amides by a 'dry' hydrolysis with phthalic acid or anhydride in the absence of water and solvent. Excellent isolated yields and selectivity (up to 99%) were attained within short reaction times (typically, 30 minutes) when the reaction was performed under microwave heating.
Relative activity of metal cathodes towards electroorganic coupling of CO2 with benzylic halides
Engelhardt, Helen,Klinkova, Anna,Medvedev, Jury J.,Medvedeva, Xenia V.
, (2021)
Electrochemical reduction of benzylic halides represents a convenient route to generating carbanions for their subsequent coupling with CO2 to obtain various carboxylic acids. Despite the industrial prospects of this synthetic process, it still lacks systematic studies of the efficient catalysts and reaction media design. In this work, we performed a detailed analysis of the catalytic activity of a series of different metal electrodes towards electroreduction of benzylic halides to corresponding radicals and carbanions using cyclic voltammetry. Specifically, we screened and summarized the performance of 12 bulk metal cathodes (Ag, Au, Cu, Pd, Pt, Ni, Ti, Zn, Fe, Al, Sn, and Pb) and 3 carbon-based materials (glassy carbon, carbon cloth, and carbon paper) towards electrocarboxylation of eight different benzylic halides and compare it to direct CO2 reduction in acetonitrile. Extensive experimental studies along with a detailed analysis of the results allowed us to map specific electrochemical properties of different metal electrodes, i.e., the potential zones related to the one- and two-electron reduction of organic halides as well as the potential windows where the electrochemical activation of CO2 does not occur. The reported systematic analysis should facilitate the development of nanostructured electrodes based on group 10 and 11 transition metals to further optimize the efficiency of electrocarboxylation of halides bearing specific substituents and make this technology competitive to current synthetic methods for the synthesis of carboxylic acids.