18454-53-0Relevant academic research and scientific papers
Superoxide Oxidation: A Novel Route to Aromatic 1,2-Dicarboxylic Acids
Sotiriou, Chariklia,Lee, Wenni,Giese, Roger W.
, p. 2159 - 2164 (1990)
Potassium superoxide in aprotic media, in the presence of 18-crown-6 ether, effects a novel and mild oxidative cleavage of quinones, cyclic alcohols, and ketones fused to various aromatic hydrocarbons.Aromatic 1,2-dicarboxylic acids are obtained as major products, with highest yields in dimethylformamide, under oxygen or air.For example, the yield of pyrene-1,2-dicarboxylic acid is 82percent from 9,10-dihydrobenzopyren-7(8H)-one and 88percent from benzopyrene-7,8-dione.Minor side products include aromatic tetrones and 3-(2-carboxyaryl)propionic or 3-(2-carboxyaryl)propenoic acid, which provide mechanistic insights.
PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS
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Paragraph 00338-00341, (2021/12/08)
The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).
Oxime-derived palladacycle Immobilized in an Ionic Liquid Brush as an Efficient and Reusable Catalyst for Mozoroki-Heck Reaction in Neat Water
Wang, Rong,Li, Shan,Li, Jing,Wei, Junfa
, (2019/09/17)
An efficient and reusable heterogeneous catalyst with oxime-derived palladacycle immobilized in an ionic liquid brush has been synthesized and an environmentally-friendly procedure have been developed for coupling aryl iodides and bromides with acrylic acid. These reactions were conducted in neat water under aerobic conditions with water-insoluble or even solid aryl halides and they proceeded smoothly and cleanly without any organic co-solvent or other additives. The ionic liquid brush could be easily recovered and reused at least five times without significant loss of activity. The protocol has the advantages of excellent yields, environmental friendliness, and catalyst recyclability.
Synthesis of o-Carboxyarylacrylic Acids by Room Temperature Oxidative Cleavage of Hydroxynaphthalenes and Higher Aromatics with Oxone
Parida, Keshaba Nanda,Moorthy, Jarugu Narasimha
supporting information, 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.
Oxidation of benzyl alcohols, benzyl halides, and alkylbenzenes with oxone
Parida, Keshaba Nanda,Jhulki, Samik,Mandal, Susovan,Moorthy, Jarugu Narasimha
, p. 9763 - 9768,6 (2020/08/20)
Oxidation of benzyl alcohols, benzyl halides, and alkylbenzenes to their corresponding oxidation products has been shown to be accomplished directly with oxone. The methodology that involves mere stirring/heating of the reactants and oxone in acetonitrile/water (1:1, v/v) is simple and practical, but is limited to substrates that do not contain sensitive functionalities and heteroaromatic rings.
IBS-catalyzed regioselective oxidation of phenols to 1,2-quinones with oxone
Uyanik, Muhammet,Mutsuga, Tatsuya,Ishihara, Kazuaki
scheme or table, p. 8604 - 8616 (2012/10/07)
We have developed the first example of hypervalent iodine(V)-catalyzed regioselective oxidation of phenols to o-quinones. Various phenols could be oxidized to the corresponding o-quinones in good to excellent yields using catalytic amounts of sodium salts of 2-iodobenzenesulfonic acids (pre-IBSes) and stoichiometric amounts of Oxone as a co-oxidant under mild conditions. The reaction rate of IBS-catalyzed oxidation under nonaqueous conditions was further accelerated in the presence of an inorganic base such as potassium carbonate (K2CO3), a phase transfer catalyst such as tetrabutylammonium hydrogen sulfate (nBu4NHSO4), and a dehydrating agent such as anhydrous sodium sulfate (Na2SO4).
Oxofunctionalized trans-2-carboxycinnamic acids by catalytic domino oxidation of naphthols and hydronaphthoquinones
Giurg, Miroslaw,Muchalski, Hubert,Kowal, Ewa
experimental part, p. 2526 - 2539 (2012/08/07)
(Chemical Equation Presented) The catalytic oxidation of naphthalenes was investigated. Hydrogen peroxide (30% aqueous) was used as an oxygen source, and 2,2′-dinitro-4,4′-ditrifluoromethyldiphenyl diselenide was the oxygen-transfer catalyst. Unsubstitute
Tandem reduction + cyclization of ortho-substituted cinnamic esters
Sass, Daiane Cristina,De Lucca Jr., Emílio Carlos,Da Silva Barbosa, Jader,De Oliveira, Kleber Thiago,Constantino, Mauricio Gomes
scheme or table, p. 5371 - 5374 (2011/10/31)
Conjugate reduction of ortho-substituted cinnamic esters by Stryker's reagent to form copper enolates, followed by intramolecular aldol-type cyclization, successfully generated indane and tetralin rings in one pot efficiently. This tandem reaction is generally diastereoselective and provides good yields.
Hydroperoxide oxidation of different organic compounds catalyzed by silica-supported selenenamide
Giurg,Brzaszcz,Mlochowski
, p. 417 - 428 (2007/10/03)
The recoverable heterogeneous silica-supported catalyst selenenamide 2 was prepared by the coupling of 3-aminopropylsilicate (4) with 2-chloroselenobenzoyl chloride (6). Its catalytic activity was demonstrated in tert-butyl hydroperoxide oxidation of aldehydes 8 to carboxylic acids 9 and benzylamines 17 to nitriles 18. Moreover, it was employed for hydrogen peroxide oxidation of azomethine compounds such as tosylhydrazones 10, oximes 13 and N,N-dimethylhydrazones 16 to parent ketones 12, arenecarboxylic acids 11 and 15, their methyl esters 14 and nitriles 18 depending on the substrate used and the reaction conditions. The catalyst was simply recovered by filtration and could be reused.
A mild and selective method for the hydrolysis of esters with trimethyltin hydroxide
Nicolaou,Estrada, Anthony A.,Zak, Mark,Lee, Sang Hyup,Safina, Brian S.
, p. 1378 - 1382 (2007/10/03)
Mild, selective, and efficient: A new method that involves the use of trimethyltin hydroxide for the hydrolysis of specific ester groups allows chemists to steer clear of unwanted elimination reactions and epimerizations. For example, the conversion of ester 1 into carboxylic acid 2 takes place under mild conditions, with nearly complete retention of stereochemical integrity. 1,2-DCE = 1,2-dichloroethane.
