Photochemical Reaction of o-Phthalaldehyde with Fullerene C60: The Stimulus for the Phthalide Additions to C60

Article abstract of DOI:10.1002/ejoc.201901363

A new, simple, and rapid photochemical reaction of o-phthalaldehyde with C₆₀ has been disclosed. This reaction afforded exclusively the unanticipated C₆₀-phthalide derivative 11 in good yield. The formation of this product is consistent with the intervention of a key free-radical intermediate –a benzylic radical– in the course of the reaction. The structure of 11 has been determined by the combined use of experimental and theoretical NMR studies. In the course of this study we further disclosed a new mode of radical reactivity of C₆₀ with a series of substituted phthalides (2, 15–17) catalyzed by tetrabutylammonium decatungstate.