579-75-9Relevant articles and documents
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Gilman et al.
, (1945)
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Synthesis of 9-ethoxycarbonyl-10(10aH)-oxo-5,6,7,8,8a,9-hexahydro-9,10a- anthracenecarbolactone and related compounds by manganese(III) mediated cyclization
Ohta, Shunsaku,Kajiura, Takahiro,Murai, Hiromichi,Yamashita, Masayuki,Kawasaki, Ikuo
, p. 2557 - 2560 (1999)
Novel tetracyclic lactone (5a), 9-ethoxycarbonyl-10(10aH)-oxo- 5,6,7,8,8a,9-hexahydro-9,10a-anthracenecarbolactone, was obtained in 34.8% yield by oxidative cyclization of diethyl trans-2-benzoylcyclohexylmalonate (4a) with manganese(III) acetate dihydrate in the presence of sodium acetate in acetic acid.
Kinetic Evidence for the Occurence of the Oxydianionic Tetrahedral Intermediates in the Hydrolyses of Methyl Salicylate and methyl o-Methoxybenzoate in Highly Alkaline Medium
Khan, M. Niyaz,Olagbemiro, T. O.
, p. 3695 - 3699 (1982)
The kinetics of hydrolyses of methyl salicylate and methyl o-methoxybenzoate have been studied at various hydroxide ion concentrations ranging from 0.01 to 4.40 M for methyl salicylate and from 0.005 to 0.200 M formethyl o-methoxybenzoate at 35 deg C.The observed rate constants are independent of -> within the range 0.01-0.04 M and vary according to equation kobsd = A + B-> + C->2 within the range 0.04-3.60 M for hydrolysis of methyl salicylate where A = k3k1/(k1 + k3),B = k2k4/(k-2 + k4), and C = k2k5K/(k-2 + k4).The observed rate constants for hydrolysis of methyl o-methoxybenzoate follow the equation kobsd = B1-> + C1->2 where B1 = k1'k2'/(k-1' + k2') and C1 = k1'k3'K'/(k-1' + k2').The pH-independent observed rate constants are 1E4 and 1E5 times larger than the corresponding values for water-catalyzed cleavages of methyl benzoate and methyl o-methoxybenzoate, respectively.This rate enhancement has been attributed to the probable intramolecular general-base-catalyzed neutral hydrolysis of methyl salicylate.The ratios B/B1 and C/C1 have been found to be 0.0214 and 0.0004, respectively.The apperance of C and C1 terms in the kinetic equations has been attributed to the existence of the oxydianionic tetrahedral intermediates in the reaction mechanisms.The temperature dependence of hydrolysis of methyl salicylate has also been studied at two differentOH- concentrations.The intramolecular general-base-catalyzed rate enhancement has been found to be due toa favorable ΔS*.The hydrolytic cleavage of methyl salicylate has been found to be sensitive to the ionic strenght.The probable mechanisms for hydrolyses of both esters are considered.
Mechanochemical Grignard Reactions with Gaseous CO2 and Sodium Methyl Carbonate**
Pfennig, Victoria S.,Villella, Romina C.,Nikodemus, Julia,Bolm, Carsten
supporting information, (2022/01/22)
A one-pot, three-step protocol for the preparation of Grignard reagents from organobromides in a ball mill and their subsequent reactions with gaseous carbon dioxide (CO2) or sodium methyl carbonate providing aryl and alkyl carboxylic acids in up to 82 % yield is reported. Noteworthy are the short reaction times and the significantly reduced solvent amounts [2.0 equiv. for liquid assisted grinding (LAG) conditions]. Unexpectedly, aryl bromides with methoxy substituents lead to symmetric ketones as major products.
Palladium-catalyzed hydrodefluorination of fluoroarenes
Brodney, Michael A.,Gair, Joseph J.,Giroux, Simon,Grey, Ronald L.
, p. 131 - 146 (2021/06/18)
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Efficiency of lithium cations in hydrolysis reactions of esters in aqueous tetrahydrofuran
Harada, Yumi,Hayashi, Kazuhiko,Ichimaru, Yoshimi,Imai, Masanori,Kojima, Yuki,Maeda, Azusa,Nakayama, Kanae,Sugiura, Kirara
, p. 581 - 594 (2021/06/06)
Lithium cations were observed to accelerate the hydrolysis of esters with hydroxides (KOH, NaOH, LiOH) in a water/tetrahydrofuran (THF) two-phase system. Yields in the hydrolysis of substituted benzoates and aliphatic esters using the various hydroxides were compared, and the effects of the addition of lithium salt were examined. Moreover, it was presumed that a certain amount of LiOH was dissolved in THF by the coordination of THF with lithium cation and hydrolyzed esters even in the THF layer, as in the reaction by a phase-transfer catalyst.
