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

摘要

The photoreactions of 4-methyl-1,2,4-triazoline-3,5-dione (NMTAD) with C_(60) and with several fullerene derivatives have been studied. In general, NMTAD cycloadds to C_(60) 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] cyclo-addition in the absence of light.