221033-72-3Relevant academic research and scientific papers
On the mechanism of the addition of organolithium reagents to cinnamic acids
Aurell, María José,Ba?uls, María José,Mestres, Ramon,Mu?oz, Elena
, p. 1067 - 1074 (2001)
The regioselectivity of the addition of tert-butyllithium to cinnamic acid is subject to reaction conditions and to substituent electronic effects. Significant effects are observed in the presence of several additives including a radical trap such as α-methylstyrene. Competition experiments by addition of the organolithium reagent to mixtures of substituted cinnamic acids show that the relative rates of both conversion of the starting acids and formation of the 1,3-adducts are subject to electronic effects, whereas rates for 1,4-addition are independent of the substituents. These features are in agreement with a polar addition mechanism, but a fast SET equilibrium followed by slow radical combination would be possible as well.
Addition of organolithium reagents to cinnamic acids
Aurell, Maria Jose,Banuls, Maria Jose,Mestres, Ramon,Munoz, Elena
, p. 831 - 846 (2007/10/03)
Reaction of tert-butyllithium with p- and m-substituted cinnamic acids at low temperature affords mixtures of 1,4- and 1,3-addition products, whose composition depend on the nature of the substituents. Electron-donating and electron-withdrawing groups favour 1,4- and 1,3-additions, respectively. Linear correlations are obtained with electronic effect and with radical substituent constants.
