Unusual C2h‐Symmetric trans‐1‐(Bis‐pyrrolidine)‐tetra‐malonate Hexa‐Adducts of C60: The Unexpected Regio‐ and Stereocontrol Mediated by Malonate–Pyrrolidine Interaction. Issue 63 (1st September 2017)

• Record Type: Journal Article
• Authors: Castro, Edison; Azmani, Khalid; Garcia, Andrea Hernandez; Aghabali, Amineh; Liu, Shuming; Metta‐Magana, Alejandro J.; Olmstead, Marilyn M.; Rodríguez‐Fortea, Antonio; Poblet, Josep M.; Echegoyen, Luis
• Is Part Of: Chemistry. Volume 23:Issue 63(2017)
• Page Start: 15937
• Page End: 15944
• Publication Date: 2017-09-01
• Subjects: fullerenes -- hexa-adducts -- malonates -- regiochemistry -- stereochemistry; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201702866
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A totally unanticipated regio‐ and stereoisomerically pure C 2h ‐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. Abstract : A totally unanticipated regio‐ and stereoselective bis‐1, 3‐dipolar cycloaddition to C60 ‐( e, e, e, e )‐tetra‐malonate is reported that leads to the formation of a pure C 2h ‐symmetric trans‐ 1‐(bis‐pyrrolidine)‐tetra‐malonate hexa‐adduct of C60 .