Functionalization of [60]Fullerene and of [60]Fullerene Monoadducts by Photochemical Cycloaddition of 4-Methyl-1,2,4-triazoline-3,5-dione

The photoreactions of 4‐methyl‐1,2,4‐triazoline‐3,5‐dione (NMTAD) with C60 and with several fullerene derivatives have been studied. In general, NMTAD cycloadds to C60 and to its monoadducts with closed structures in a highly regioselective [2+2] fashion at a cis‐1 [6,6] double bond. Cycloadditions to azafulleroids occur by a slightly different pathway and result in partially cluster‐opened bis(adducts). 1,6‐Methano[60]fulleroid, however, also undergoes a [2+2+2] cycloaddition in the absence of light. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)