Regioselective triphenylamine-tether-directed synthesis of [60]fullerene bis-adducts

Abstract

The tether-directed regioselective synthesis of equatorial bis-adducts of [60]fullerene via the 1,3-dipolar cycloaddition reaction of azomethine ylides is reported. A mono-[60]fulleropyrrolidine adduct, derived via 1,3-dipolar cycloaddition of azomethine ylides generated in situ upon thermal condensation of triphenylarnine bis-aldehyde and an alpha-amino acid, was isolated and further reacted to yield, exclusively and selectively, the equatorial bis-adduct, which is structurally characterized by appropriate spectroscopic means.