SYNTHESIS OF PYRROLIDINE RING-FUSED FULLERENE MULTICARBOXYLATES BY PHOTOREACTION

Aminopolycarboxylic esters react with C-60 under photolysis to produce fullerene multicarboxylates. Irradiation of tetramethyl ethylenediami netetraacetate (EDTA) with C-60 yields the EDTA-containing fullerene m onoadduct C-60(MeOOCCH)(2)NCH2CH2N(CH2COOMe)(2). In addition, several other C-60 monoadducts are also isolated and characterized, including compounds due to EDTA fragmentation. Similar results are observed with pentamethyldimethylenetriaminepentaaceta (DTPA). When partially methy lated nitrilotriacetic acid is irradiated with C-60, decarboxylation o ccurs and organo dihydrofullerene derivatives such as C-60(H)(CH2N(CH2 COOMe)(2)) are formed. Radical mechanisms are proposed for both types of photoreactions. The fullerene derivatives are characterized by thei r spectroscopic data. Photoreactions of C-60 with other analogous mole cules also support the conclusions.