Intramolecular General Base Catalyzed Ester Hydrolysis. The Hydrolysis of 2-Aminobenzoate Esters

2002 ◽  
Vol 67 (10) ◽  
pp. 3179-3183 ◽  
Author(s):  
Thomas H. Fife ◽  
Randhir Singh ◽  
Ramesh Bembi
1982 ◽  
Vol 35 (7) ◽  
pp. 1357 ◽  
Author(s):  
TJ Broxton

The hydrolysis of 2-acetyloxybenzoic acid in the pH range 6-12 has been studied in the presence of micelles of cetyltrimethylammonium bromide (ctab) and cetylpyridinium chloride (cpc). In the plateau region (pH 6-8) the hydrolysis is inhibited by the presence of micelles, while in the region where the normal BAC2 hydrolysis (pH > 9) occurs the reaction is catalysed by micelles of ctab and cpc. The mechanism of hydrolysis in the plateau region is shown to involve general base catalysis by the adjacent ionized carboxy group both in the presence and absence of micelles. This reaction is inhibited in the presence of micelles because the substrate molecules are solubilized into the micelle and water is less available in this environment than in normal aqueous solution.


1988 ◽  
Vol 43 (12) ◽  
pp. 1662-1671 ◽  
Author(s):  
Hans Möhrle ◽  
Wolfgang Vetter

Abstract Aminomethanephosphonate. Mercury EDTA Dehydrogenation. Lactam. Formamide, Aminoalkylation Aminophosphonates 1-5 are dehydrogenated with mercury EDTA to the corresponding lactams 6-9 and surprisingly to the formamide derivative 10, The different rate of ester hydrolysis of these acylamine compounds, the steric requirements and the reaction mechanisms are dis-cussed.


2011 ◽  
Vol 133 (45) ◽  
pp. 18452-18462 ◽  
Author(s):  
Marie Lopez ◽  
Hoan Vu ◽  
Conan K. Wang ◽  
Maarten G. Wolf ◽  
Gerrit Groenhof ◽  
...  

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