Synthesis of [70]Azafulleroids:  Investigations of Azide Addition to C₇₀

Abstract

Treatment of C 70 with (2-methoxyethoxy)methyl azide gives rise to three out of a possible six triazoline isomers, showing chemoselectivity as well as regioselectivity. The major product arose from addition of azide to the double bond of C 70 possessing the greatest local curvature. Selective thermolysis of the least stable triazoline, the one resulting from addition to the least curved [6,6] double bond, allowed solution of the structure of the three isomers. Thermolysis of the triazoline isomers produced mixtures of C 70, azafulleroids, and fulleroaziridines.