Unusual C2h -Symmetric trans-1-(Bis-pyrrolidine)-tetra-malonate Hexa-Adducts of C60 : The Unexpected Regio- and Stereocontrol Mediated by Malonate-Pyrrolidine Interaction.
Edison CastroKhalid AzmaniAndrea Hernandez GarciaAmineh AghabaliShuming LiuAlejandro J Metta-MaganaMarilyn M OlmsteadAntonio Rodríguez-ForteaJosep M PobletLuis A EchegoyenPublished in: Chemistry (Weinheim an der Bergstrasse, Germany) (2017)
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 1 H and 13 C 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.