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A totally unanticipated regio- and stereoisomerically pure C2h-symmetric trans-1-(bis-pyrrolidine)-tetra-malonate hexa-adduct of C60 was obtained via a topologically controlled method, followed by a 1,3-dipolar cycloaddition reaction. The structures of the products were elucidated by 1H and 13C NMR and by X-ray crystallography. The unexpected regio- and stereoselectivity observed, supported by theoretical calculations, was found to be a consequence of malonate–pyrrolidine interactions.
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Manuscript title: Unusual C2h-Symmetric trans-1-(Bis-pyrrolidine)-tetra-malonate Hexa-Adducts of C60: The Unexpected Regio- and Stereocontrol Mediated by Malonate–Pyrrolidine Interaction
Journal: Chem. Eur. J.