6533b82dfe1ef96bd12908c7

RESEARCH PRODUCT

Addition of organolithium reagents to cinnamic acids

Elena MuñozRamon MestresMaría José AurellMaría-josé Bañuls

subject

chemistry.chemical_compoundchemistryReagentOrganic ChemistryDrug DiscoverySubstituentButyllithiumElectronic effectOrganic chemistryComposition (visual arts)Biochemistry

description

Abstract 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.

https://doi.org/10.1016/s0040-4020(98)01074-6