83624-76-4Relevant academic research and scientific papers
Reactivity of Some Cyclohexanol Derivatives towards Sodium Ethoxide in Ethanol
Darwish, A. I.
, p. 695 - 711 (2007/10/03)
Two series of 2-(p-aroyl)-1,3,5-tri (p-aryl)-4-carbethoxy-4-cyanocyclohexan-1-ols IIa-f and IIg-h were prepared and the structure of the new compounds IIf,g,i was established by elemental analysis and spectroscopic methods. These cyclohexanol derivatives IIa-f and IIg-k were allowed to react with sodium ethoxide in absolute ethanol afforded the corresponding trans-1,3-di-(p-aryl)-2-propenones Ia-f and Ig-k, respectively besides ethyl cyanoacetate as a bi-product. The reaction kinetics has been studied spectrophotometrically at three different temperatures and the observed rate constants were calculated. Cood Hammett correlations with ρ values of series IIa-f ranged between 0.76 and 1.34, whereas of series IIg-k they were between 1.01 and 1.54 which suggest a carbanionic character of the transition states. The values of thermodynamic parameters ΔH(act.) and ΔS(act.) confirmed the proposed multi-step mechanism.
