Selective deletion of one carbon atom from C60 through benzylamine mediated reactions

Abstract

Selective deletion of carbon atom(s) from spherical skeletons results in norfullerene derivatives. Among the numerous fullerene derivatives, norfullerenes are still quite rare. In the present work benzylamine has been found to react with a [60]fullerene-mixed peroxide derivative with a 9-membered orifice. Subsequent transformations of the benzylamine-added product afforded a nor[59]fullerene derivative with an 11-membered orifice. The carbon atom deletion process involves an intramolecular hydrogen atom transfer and decarboxylation sequence.