Regioselective addition of Grignard reagents to tosylazafulleroid and derivatization to 1,2-disubstituted [60]fullerene

Abstract

Grignard reagents (RMgBr: R = Et, p-tolyl) selectively attacked the β-position of the bridgehead double bond of tosylazafulleroid through interaction of Mg with the SO group. The following [5,6] ring closure and C–N bond scission led to aryl/alkyl aminylfullerenes with 1,2-configuration. Tolyl-substituted aminylfullerene was further converted into 1,4-di(p-tolyl)fullerene on treatment in acidic toluene.