1523-13-3Relevant articles and documents
Reactions of aryl benzoates with potassium aryloxides: Solvent effects on reaction pathway and kinetics
Khalfina, Irina A.
, p. 302 - 314 (2015)
Temperature dependences of the relative reactivity of potassium aryloxides XC6H4O-K+ toward 2,4-dinitrophenyl benzoate in 50 mol% dimethylformamide (DMF)-50 mol% H2O mixture have been studied using the competitive reactions technique. Correlation analyses of the relative rate constants kX/kH and differences in the activation parameters (ΔΔCyrillic capital letter en≠ and ΔΔS≠) of the competitive reactions have revealed the existence of two isokinetic series of the reactions of 2,4-dinitrophenyl benzoate with potassium aryloxides with electron-donating substituent (EDS) and electron-withdrawing substituent (EWS), respectively. We have investigated the effect of the substituent X on the activation parameters for each isokinetic series and concluded that the mechanism of the reactions of 2,4-dinitrophenyl benzoate with potassium aryloxides XC6H4O-K+ in 50 mol% DMF-50 mol% H2O mixture is the same as in DMF. Analysis of the obtained data with using the method of two-dimensional reaction coordinate diagram leads to the conclusion that the variation of the solvent from DMF to 50 mol% DMF-50 mol% H2O mixture affects the reaction pathway. The rate constant kX for the reaction of 3-nitrophenyl benzoate with potassium 4-methoxyphenoxide and the relative rate constants kX/kH for the reaction of 3-nitrophenyl benzoate with potassium aryloxides XC6H4O-K+ with EDS were measured in 50 mol% DMF-50 mol% H2O mixtures at 25C, and it has been shown that the addition of water to DMF does not change the mechanism but slows down these reactions.
Electrodimerization of N-Alkoxyamides for Zinc(II) Catalyzed Phenolic Ester Synthesis under Mild Reaction Conditions
Subramanian, Kripa,Yedage, Subhash L.,Bhanage, Bhalchandra M.
, p. 2511 - 2521 (2018/05/14)
An electrochemical On-Off method for phenolic ester synthesis from N-alkoxyamides has been reported. This one-pot protocol begins with rapid and selective electrodimerization of the amide using n-Bu4NI (TBAI) as an electrocatalyst. The reaction proceeds further in the absence of current via Zn catalyzed C?N bond activation of the amide dimer followed by its coupling with phenol to form the ester. The present methodology is ligand-free and takes place under mild reaction conditions. This transformation incorporates a wide variety of phenols and amide substrates leading to the formation of functionalized esters highlighting its versatility. (Figure presented.).
Ph3P-I2 mediated aryl esterification with a mechanistic insight
Phakhodee, Wong,Duangkamol, Chuthamat,Pattarawarapan, Mookda
supporting information, p. 2087 - 2089 (2016/04/26)
In order to better understand the reaction mechanism and to obtain optimal conditions, the Ph3P-I2/Et3N mediated aryl esterification reaction was thoroughly investigated. Using a specific reagent addition sequence, the reaction proceeds remarkably well especially with acidic substrates. 31P NMR studies revealed that the formation of an aryloxyphosphonium salt is crucial in governing the reaction path toward the formation of phenolic esters.
