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

✍ Scribed by Georgios Rotas; Nikos Tagmatarchis

• Book ID: 104096014
• Publisher: Elsevier Science
• Year: 2009
• Tongue: French
• Weight: 284 KB
• Volume: 50
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.11.022

✦ Synopsis

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 triphenylamine bis-aldehyde and an a-amino acid, was isolated and further reacted to yield, exclusively and selectively, the equatorial bis-adduct, which is structurally characterized by appropriate spectroscopic means.