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Studies on the Toxic Oil Syndrome: proposal of a mechanism for the thermal conversion of 3-N-phenylamino-1,2-propanediol esters into anilides under deodorisation conditions
|Authors:||Escabrós, Jordi; Crehuet, Ramón ; Messeguer Peypoch, Ángel|
|Keywords:||Toxic Oil Syndrome|
|Citation:||Tetrahedron 65(1): 418-426 (2009)|
|Abstract:||A study on the reaction mechanism for the conversion of title esters, the species recognised as toxic biomarkers of the oil batches responsible for the Toxic Oil Syndrome, into the corresponding anilides under the thermal conditions of an oil deodorisation process was performed using experimental and computational techniques. The results obtained suggest a reaction course that includes two basic steps: an intramolecular process involving the reaction of the amine group of the diester derivative with the secondary ester of the same compound, followed by the attack of an aniline molecule to form the (E)-isomer of an imidic acid, which would finally tautomerise to give the final anilide.|
|Description:||9 pages, 4 figures.-- Supplementary information (Schemes S1-S2, figure S1, tables S1-S2 and suppl. data, 4 pages) available at the paper site.|
Available online 10 October 2008.
|Publisher version (URL):||http://dx.doi.org/10.1016/j.tet.2008.09.102|
|Appears in Collections:||(IQAC) Artículos|
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