73005-48-8Relevant academic research and scientific papers
Synthesis, characterization and applications of polymer-metal chelates derived from poly[((4-acryloxy acetophenone)-divinylbenzene)] benzoyl hydrazone resins
Ravi Sankar, Thammisetty,Kesavulu,Venkata Ramana, Peddakotla
, p. 597 - 608 (2014)
4-Acryloxy acetophenone was prepared and subjected to suspension polymerization with divinylbenzene as a cross-linking agent. The resulting network polymer was ligated with benzoyl hydrazone. The functional polymer was treated with metal ions [Cu(II), Fe(
Control of the 'Extended' E1cB Mechanism of Acyl Group Transfer in Activated Esters of Acrylic Acids
Douglas, Kenneth T.,Williams, Andrew
, p. 131 - 134 (2007/10/02)
Aminolysis and alkaline hydrolysis of aryl propenoates are shown to proceed via a normal nucleophilic substitution mechanism.The 'extended' E1cB mechanism of hydrolysis involving attack of hydroxide ion at the β-carbon followed by expulsion of the phenolate ion from the resulting carbanion is shown not to occur with the parent propenoate.The 'extended' E1cB mechanism is taken by the hydrolysis of 2-cyano-3-(4-methoxyphenyl)propenoate esters due to the stabilising effect of the cyano-group on the intermediate carbanion.
Dehydrobromination of Some Substituted Phenyl 3-Bromopropionates and Phenyl 3-Bromothiolopropionates. Transmission of Activation Effects through Acyl Bonds
Gilbert, Arthur B.,Peters, Frances B.,Johnson, H. W.
, p. 2724 - 2728 (2007/10/02)
Thirteen aryl 3-bromopropionates and nine aryl 3-bromothiolopropionates were prepared and subjected to dehydrohalogenation with sodium 3,4-dinitrophenoxide in dry tetrahydrofuran at 34.25 deg C.The second-order rate constants for the sulfur esters were approximately 10 times those for the corresponding oxygen esters.Good Hammett plots with ρ's of +0.81+/-0.04 and 0.98+/-0.04 for the oxygen and sulfur series, respectively, were obtained by using ?n.Activation parameters were measured for two oxygen and two sulfur esters; in both bases, low (12-13 kcal/mol) activatio n enthalpies and moderately large negative (19-21 eu) activation entropies were found.At 34.25 deg C, 3'-nitrophenyl 3-bromopropionate dehydrohalogenated 14 times more rapidly than 3'-nitrophenyl 3-chloropropionate; phenyl 3-bromothiolopropionate dehydrohalogenated 11 times more rapidly than the phenyl 3-chlorothiolopropionate.The rate constant ratio for 4'-bromophenyl 3-bromopropionate vs. 4'-bromophenyl 3-bromopropionate-2-d was 1.84; the monodeuterated compound yielded olefinic product with 65percent D.H was abstracted preferentially from 4'-chlorophenyl 3-bromothiolopropionate partially deuterated in the 2-position, but no kinetic results were obtained.No evidence of reversibility was found with 2,4-dinitrophenol-d, and the addition of 2,4-dinitrophenol to kinetic mixtures had essentially no effect on the rate conatants.The results are interpreted to indicate an E2 process near the EL/E1cB borderline with the thiolo ester deviating somewhat more toward an E1cB-I process.
