Synthesis, structures, and properties of new thiophosphorylated fullerenopyrrolidines. First example of the Pishchimuka reaction in fullerene derivatives

Abstract

The reactions of fullerene C 60 with thiophosphorylated mono or dialdehydes and N methylglycine in toluene afforded new thiophosphorylated fullerenopyrrolidines, including those containing the free aldehyde group. The purity and compositions of the reaction products were confirmed by MALDI TOF mass spectrometry and HPLC. The structures of the reaction products were established by two dimensional homo and heterocorrelation NMR experi ments. The properties of the products were studied by cyclic voltammetry and quantum chemi cal methods. The Pishchimuka rearrangement in thiophosphorylated derivatives of fullereno pyrrolidines was performed for the first time, and thiol esters of phosphonic acids of fullerenopyrrolidines were prepared.