93979-11-4Relevant academic research and scientific papers
KINETICS OF THE DECOMPOSITION OF 1-ARYL-2,2,2-TRIHALOGENOETHANOLS IN AQUEOUS BASE
Lins, Hilvania Silva e,Nome, Faruk,Rezende, Marcos Caroli,Sousa, Iolanda de
, p. 1521 - 1526 (2007/10/02)
The decomposition of several 1-aryl-2,2,2-trichloro- and 1-aryl-2,2,2-tribromo-ethanols in aqueous base is studied.The title compounds yield the corresponding benzaldehydes and the halogenoform with base.The kinetics are compatible with an (E1cB)R mechanism.Values for the rates of collapse of the intermediate alkoxides and for the pKa values of all ethanols are estimated.Electron-donating substituents on the ring facilitate decomposition and decrease the acidity of the ethanols.Solvent isotope effects, kH2O/kD2O, for the reactions are small.The absence of mandelic acid derivatives among the products, in apperent disagreetment with other related studies, is discussed and justified in the light of a scheme which reconciles previous conflicting observations found in the literature.
