ISOMERIC FLUOROBENZYL AND FLUOROTROPYLIUM CATIONS

Article abstract of DOI:10.1016/S0022-1139(00)82656-1

The tendency for isomerization of toluene and cycloheptatriene molecular ions, and of benzyl and tropylium product ions, is substantially reduced by fluorine substitution, irrespective of position.This stabilization appears to be due to back-donation of electrons from fluorine, despite its high electronegativity.