Bridged aromatic alkenes for the study of carbocation-π interaction

Toward the goal of gaining further insight into carbocation-π interactions, bridged-ring aromatic alkene model systems are being investigated in which one isomer will permit π complexation of an intramolecular tertiary carbocation with a benzene ring, but the other isomer will not. The syntheses of three sets of such isomers, having, respectively, benzobicyclo[3.2.1]octene, benzobicyclo[2.2.1]heptene, and benzobicyclo[4.2.1]nonene structures, are described.

Graphical abstractThree pairs of isomeric bridged-ring alkenes have been synthesized for planned studies of carbocation-π interaction by comparison of the stabilities of the cations formed by protonation.Download full-size image