6533b838fe1ef96bd12a45cf
RESEARCH PRODUCT
On the mechanism of the addition of organolithium reagents to cinnamic acids
Ramon MestresMaría-josé BañulsMaría José AurellElena Muñozsubject
Reaction conditionsChemistryOrganic ChemistrySubstituentRegioselectivitychemistry.chemical_elementOrganolithium reagentBiochemistryMedicinal chemistryCinnamic acidchemistry.chemical_compoundReagentDrug DiscoveryElectronic effectOrganic chemistryLithiumdescription
Abstract 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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2001-02-01 | Tetrahedron |