Electrochemical Formation of Oxazolines by 1,3-Oxyfluorination of Non-activated Cyclopropanes
Madara Da̅rziņa, Aigars Jirgensons
Abstract
The C–C bond in non-activated cyclopropanes can be intramolecularly cleaved with an electrochemically generated amidyl radical forming oxazolines. In the presence of TBABF 4, this provides 1,3-oxyfluorination products. C–C bond cleavage of cyclopropane proceeds with inversion of the configuration, suggesting an intramolecular homolytic substitution (S H i) mechanism. The performance of TBABF 4 as an efficient fluoride source was explained by accumulation of the BF 4 – anion at the anode surface, at which a carbocation is formed by the oxidation of the C-centered radical.
Topics & Concepts
ChemistryCyclopropaneHomolysisIntramolecular forceCarbocationBond cleavageElectrochemistryWalden inversionFluoridePhotochemistryRadical ionElectrosynthesisMedicinal chemistryCleavage (geology)IonStereochemistryOrganic chemistryRadicalCatalysisInorganic chemistryRing (chemistry)ElectrodePhysical chemistryGeotechnical engineeringFracture (geology)EngineeringCyclopropane Reaction MechanismsFluorine in Organic ChemistryCatalytic C–H Functionalization Methods