Addition of organolithium reagents to cinnamic acids

Article abstract of DOI:10.1016/S0040-4020(98)01074-6

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.